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5
[Br-].C[Mg+].N1N=C(C=C1)C(=O)OCC>C1CCCO1>N1N=C(C=C1)C(C)(C)O
3
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[N:22][CH:23]=3)[CH:10]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[N:12]=2)=[CH:4][CH:3]=1.[NH2:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][CH:29]=[CH:28][N:27]=1.C([O-])([O-])=O.[Cs+].[Cs+].[I-]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.O1CCOCC1>[CH3:24][C:21]1[N:22]=[CH:23][C:18]([N:9]2[CH:10]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[N:12]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([NH:25][C:26]3[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:3][CH:4]=2)=[CH:19][CH:20]=1
2
C(C)(C)(C)OC(N(CCNC(C(F)(F)F)=O)CCCC1=CC=C(C=C1)[N+](=O)[O-])=O>O.CO[H].C([O-])([O-])=O.[K+].[K+]>C(C)(C)(C)OC(N(CCCC1=CC=C(C=C1)[N+](=O)[O-])CCN)=O
3
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([OH:21])[C@H:12]([NH:15][C:16]([CH:18]([Cl:20])[Cl:19])=[O:17])[CH2:13][OH:14])=[CH:9][CH:10]=1)(=[O:4])=[O:3].CO[C:24](OC)([CH3:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:19][CH:18]([Cl:20])[C:16]([N:15]1[C@H:12]([CH2:13][OH:14])[C@@H:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)[O:21][C:24]1([CH3:26])[CH3:25])=[O:17]
2
[C:1]1([C:7](=[N:14][NH2:15])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.CN(C)C(N(C)C)=N.C(OO)(=O)C>ClCCl>[C:1]1([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:14]=[N-:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
1
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[CH2:29][CH2:28][CH2:27]2.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:22])[NH:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[CH2:29][CH2:28][CH2:27]4)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
1
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH2:11]([P:18]([NH:27][C@H:28]([C:30]([N:32]1[CH2:46][CH2:45][CH2:44][C@H:33]1[C:34]([N:36]1[CH2:43][CH2:42][CH2:41][C@H:37]1[C:38]([OH:40])=[O:39])=[O:35])=[O:31])[CH3:29])([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH2:11]([P:18]([NH:27][C@H:28]([C:30]([N:32]1[CH2:46][CH2:45][CH2:44][C@H:33]1[C:34]([N:36]1[CH2:43][CH2:42][CH2:41][C@H:37]1[C:38]([OH:40])=[O:39])=[O:35])=[O:31])[CH3:29])([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
1
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][N:27]2[C:35]3[C:30](=[CH:31][C:32]([C:36]4[CH:37]=[N:38][N:39]([CH:41]5[CH2:46][CH2:45][CH2:44][CH2:43][O:42]5)[CH:40]=4)=[CH:33][CH:34]=3)[CH:29]=[CH:28]2)[CH2:22][CH2:21]1.[CH2:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(=O)(O)[O-].[Na+]>ClCCl.CO.ClCCl>[CH2:47]([NH:54][C:5]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][N:27]2[C:35]3[C:30](=[CH:31][C:32]([C:36]4[CH:37]=[N:38][N:39]([CH:41]5[CH2:46][CH2:45][CH2:44][CH2:43][O:42]5)[CH:40]=4)=[CH:33][CH:34]=3)[CH:29]=[CH:28]2)[CH2:22][CH2:21]1)=[O:11])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1
2
FC1=C(OCCN2CCC(CC2)(C(=O)OCC)CCCC2=C(C=NC3=CC=C(C=C23)OC)F)C(=CC=C1)F>CO[H].[OH-].[Na+].O1CCOCC1>FC1=C(OCCN2CCC(CC2)(C(=O)O)CCCC2=C(C=NC3=CC=C(C=C23)OC)F)C(=CC=C1)F
3
[N+](=O)([O-])C1=CC=C(COC(C(Cl)N2C([C@@H]([C@H]2SC(C)=O)OC)=O)=O)C=C1>C1CCCO1.c3c(P(c1ccccc1)c2ccccc2)cccc3.ClCCl>[N+](=O)([O-])C1=CC=C(COC(C(=P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)N2C([C@@H]([C@H]2SC(C)=O)OC)=O)=O)C=C1
3
Cl.[N+:2]([C:5]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])([O-])=O>C(O)C>[NH2:2][C:5]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]
1
Cl[C:2]1[C:3]2[C:4](=[CH:13][N:14](CC3C=CC(OC)=CC=3)[N:15]=2)[N:5]=[C:6]([C:8]2[N:9]=[CH:10][O:11][CH:12]=2)[N:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][N:35]([C:38](=[O:40])[CH3:39])[CH2:34][CH2:33]2)=[CH:28][CH:27]=1.Cl>CO.O1CCOCC1>[O:11]1[CH:12]=[C:8]([C:6]2[N:7]=[C:2]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:33][CH2:34][N:35]([C:38](=[O:40])[CH3:39])[CH2:36][CH2:37]4)=[CH:30][CH:31]=3)[C:3]3[NH:15][N:14]=[CH:13][C:4]=3[N:5]=2)[N:9]=[CH:10]1
2
ClC1=CN=C(C(=N1)N)SC=1C(=NC=CC1)Cl.CC(C)(C)[S@@](=O)N[C@@H]1CCCC12CCNCC2>C(C)(C)N(C(C)C)CC>NC1=C(N=CC(=N1)N1CCC2(CCC[C@H]2N[S@](=O)C(C)(C)C)CC1)SC=1C(=NC=CC1)Cl
3
C[O:2][C:3](=[O:14])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[N:8]=1.[OH-].[Li+]>CO>[Br:13][C:9]1[N:8]=[C:7]([CH2:6][O:5][CH2:4][C:3]([OH:14])=[O:2])[CH:12]=[CH:11][CH:10]=1
1
[CH3:1][O:2][C:3](=[O:29])[CH:4]=[C:5]([OH:28])[CH2:6][CH:7]([C:9]1[N:10]([CH:25]([CH3:27])[CH3:26])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5](=[O:28])/[CH:6]=[CH:7]/[C:9]1[N:10]([CH:25]([CH3:26])[CH3:27])[C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2
1
NC1=CC=C(C(=O)OC(C)(C)C)C=C1.ClC1=NC(=NC(=N1)Cl)OCC(F)(F)F>C1CCCO1>ClC1=NC(=NC(=N1)OCC(F)(F)F)NC1=CC=C(C(=O)OC(C)(C)C)C=C1
3
C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.[N+](=O)([O-])C1=CC=C2CCNCC2=C1>O.[OH-].[Na+].O1CCOCC1>C(C)(C)(C)OC(=O)N1CC2=CC(=CC=C2CC1)[N+](=O)[O-]
3
N(=[N+]=[N-])\C(\C(=O)OC)=C/C1=C(C=CC=C1)Cl>C1(=CC=CC=C1)C>ClC1=C2C=C(NC2=CC=C1)C(=O)[O-]
4
ClS(=O)(=O)O.FC1=CC=C(C=C1)N1N=CC=C1>>FC1=CC=C(C=C1)N1N=CC(=C1)S(=O)(=O)Cl
5
FC(C1=C(CO)C=CC=C1)(F)F.ClC1=NC(=NC(=N1)Cl)NC1=CC=C(C=C1)C(F)(F)F>CC#N.[H-].[Na+]>FC(C1=C(COC2=NC(=NC(=N2)OCC2=C(C=CC=C2)C(F)(F)F)NC2=CC=C(C=C2)C(F)(F)F)C=CC=C1)(F)F.ClC1=NC(=NC(=N1)OCC1=C(C=CC=C1)C(F)(F)F)NC1=CC=C(C=C1)C(F)(F)F
3
[O:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.O=[O+][O-].[NH2:9][CH2:10][C:11]([F:38])([F:37])[CH2:12][NH:13][C:14](=[O:36])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][CH2:23][C:24]2[S:28][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[N:26][CH:25]=2)[CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)Cl>[F:38][C:11]([F:37])([CH2:10][N:9]1[CH2:4][CH2:5][O:1][CH2:2][CH2:3]1)[CH2:12][NH:13][C:14](=[O:36])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][CH2:23][C:24]2[S:28][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[N:26][CH:25]=2)[CH:16]=1
1
[N:1]([C:4]1[S:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[C:7]([CH3:9])[N:8]=1)=[N+:2]=[N-:3].C(N(CC)C(C)C)(C)C.[C:29]([O:33][CH2:34][CH3:35])(=[O:32])[C:30]#[CH:31]>O1CCCC1.[Cu]I>[CH2:13]([NH:12][C:10]([C:6]1[S:5][C:4]([N:1]2[CH:31]=[C:30]([C:29]([O:33][CH2:34][CH3:35])=[O:32])[N:3]=[N:2]2)=[N:8][C:7]=1[CH3:9])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
1
ClC1=C(C=NN(C1=O)CC(=O)NCC1=C(C=NC=C1)O)N[C@H]1[C@@H]([C@@H]2C([C@H](C1)C2)(C)C)C>>ClC1=C(C=NN(C1=O)CC(=O)NCC1=C(C=NC=C1)OC(C)C)N[C@H]1[C@@H]([C@@H]2C([C@H](C1)C2)(C)C)C
5
C[Si](C)(C)Cl.NC=1C=C2CCC(N(C2=CC1)C)=O.ClC=1N=C(C2=C(N1)N(C=C2C2=CC=C(C=C2)F)S(=O)(=O)C2=CC=C(C)C=C2)NC2CC2>C(CCC)O>NC=1C2=C(N=C(N1)NC=1C=C3CCC(N(C3=CC1)C)=O)NC=C2C2=CC=C(C=C2)F
3
C1(=CC=CC=C1)S(=O)(=O)Cl.N1C=CC=2C(=CC=CC12)C=O>O.ClCCl.[OH-].[Na+].S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC>C1(=CC=CC=C1)S(=O)(=O)N1C=CC=2C(=CC=CC12)C=O
3
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2O.P(Cl)(Cl)([Cl:15])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:15][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1
1
NC1=[N+](C=CN=C1C(=O)OC)[O-]>N(C)(C)C=O.P(=O)(Cl)(Cl)Cl>COC(=O)C1=NC=C(N=C1N)Cl
3
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].C1=C(C=CC2=CC=CC=C12)C=1CC2CN(C3=C(C(N2C1)=O)C=C(C(=C3)OC)OC)COCC[Si](C)(C)C>C1CCCO1.CCO[H]>COC=1C(=CC2=C(C(N3[C@H](C=N2)CC(=C3)C3=CC2=CC=CC=C2C=C3)=O)C1)OC
3
COC(OC)=O.C(C)(=O)OC1=CC=CC=C1>C[O-].[Ti+4].C[O-].C[O-].C[O-]>C1(=CC=CC=C1)OC(OC1=CC=CC=C1)=O.C(OC1=CC=CC=C1)(OC)=O
3
BrCCCO[Si](C)(C)C(C)(C)C.ClC1=NC=2N(C(NC(C2N1CC=C)=O)=O)CC>N(C)(C)C=O.C([O-])([O-])=O.[K+].[K+].[I-].C(CCC)[N+](CCCC)(CCCC)CCCC>C(C=C)N1C(=NC=2N(C(N(C(C12)=O)CCCO[Si](C)(C)C(C)(C)C)=O)CC)Cl
3
NC=1C=CC=C2C=CC=NC12.C(=O)(OC(C)(C)C)N1[C@H](C(=O)O)CCC1>>C(C)(C)(C)OC(=O)N1[C@@H](CCC1)C(NC=1C=CC=C2C=CC=NC12)=O
5
C(=O)C=O.BrC1=CC(=C(C(=C1)N)N)OCC1=CC=C(C=C1)OC>CCO[H]>BrC1=CC(=C2N=CC=NC2=C1)OCC1=CC=C(C=C1)OC
3
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[CH:14]1([CH:20]=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:20]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[OH:21])=[CH:3][CH:4]=1
1
C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.BrC1=CC=CC=2NC=NC21>ClCCl.C(C)(C)N(C(C)C)CC>BrC1=CC=CC2=C1N(C=N2)C(=O)OC(C)(C)C
3
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=[O:11].[OH-].[K+].[CH3:17][C:18]1([O:21][CH2:20]1)[CH3:19].Cl>CS(C)=O.C(OCC)(=O)C.O>[OH:21][C:18]([CH3:20])([CH3:19])[CH2:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11]
1
[CH3:1][C:2]1([CH3:39])[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si](CC(C)C)(C)C)=[CH:14][CH:13]=2)[C:8]2[CH:7]=[C:6]([C:26]#[C:27][C:28]3[CH:38]=[CH:37][C:31]([C:32]([O:34]CC)=[O:33])=[CH:30][CH:29]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>CCO.C1COCC1>[CH3:1][C:2]1([CH3:39])[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:8]2[CH:7]=[C:6]([C:26]#[C:27][C:28]3[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:37][CH:38]=3)[CH:5]=[CH:4][C:3]1=2
1
CC[Mg+].[Br-].CC1=C(C=CC(=C1)F)C=1C2=C(N=C(N1)SC)N(C=C2C#N)COCC[Si](C)(C)C>[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>C(C)C=1N=C(C2=C(N1)NC=C2C#N)C2=C(C=C(C=C2)F)C
3
OC=1C=C(C(=O)O)C=CC1.N1(CCNCC1)C(=O)OCC1=CC=CC=C1>ClCCl.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C>OC=1C=C(C(=O)N2CCN(CC2)C(=O)OCC2=CC=CC=C2)C=CC1
3
N[C@H](CN1N=C(C=C1)C1=CC(=C(C#N)C(=C1)F)Cl)C.O1N=C(C=C1)C1=NC(=NO1)C(=O)O>>ClC=1C=C(C=C(C1C#N)F)C1=NN(C=C1)C[C@H](C)NC(=O)C1=NOC(=N1)C1=NOC=C1
5
FC=1C=C2C(=CC=C(C2=CC1)N1C[C@H](NCC1)C)I>>C(#N)C1=CC=C(C2=CC=C(C=C12)F)N1C[C@H](NCC1)C
5
COC=1C=C(N)C=CC1OC.C(C)(C)(C)[Si](O[C@@H]1CC[C@H](CC1)N1C(N(CC=2C1=NC(=NC2)Cl)C2=C(C=C(C=C2)OC)F)=O)(C)C>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.CC(C)O>FC1=C(C=CC(=C1)OC)N1C(N(C2=NC(=NC=C2C1)NC1=CC(=C(C=C1)OC)OC)[C@@H]1CC[C@H](CC1)O)=O
3
F[C@@H]1[C@@H](C1)C(=O)NC1=CC=C2C(=N1)N(N=C2C=2C(=NC=CC2C)OC)COCC[Si](C)(C)C>CC#N.ClCCl.C(=O)(C(F)(F)F)O>F[C@@H]1[C@@H](C1)C(=O)NC1=CC=C2C(=N1)NN=C2C=2C(=NC=CC2C)OC
3
ClC(C(=O)N1CCN(CC1)C1=C(C=CC(=C1)S(=O)(=O)N1C=CC2=CC=C(C=C12)Br)OC)(Cl)Cl>C1CCCO1.[OH-].[K+]>BrC1=CC=C2C=CN(C2=C1)S(=O)(=O)C1=CC(=C(C=C1)OC)N1CCNCC1
3
NC1=C(C=CC=C1OC)O>C1(=CC=CC=C1)C.C(CC)(=O)O>OC1=C(C=CC=C1)NC(CCOC)=O
3
BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3=CC=C(C=C3)OC)CN(C(C)=O)CC>O(O[H])[H].ClCCl.ClC=1C=C(C(=O)OO)C=CC1.C(O)([O-])=O.[Na+]>BrC=1C=CC=2C3=C(C=[N+](C2C1)[O-])N=C(N3CC3=CC=C(C=C3)OC)CN(C(C)=O)CC
3
C(C(C)=C)Cl.CC1=C(C=C2CC[C@@](OC2=C1C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O>C([O-])([O-])=O.[K+].[K+].CC(=O)C.[I-].[Na+]>C[C@@]1(OC2=C(C(=C(C=C2CC1)OCC(=C)C)C)C)CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C
3
I[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][CH:3]=1.N1CCCCC1.[O:25]1[CH:29]=[C:28]([C:30]([OH:34])([C:32]#[CH:33])[CH3:31])[N:27]=[CH:26]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[NH2:17][C:13]1[N:12]=[C:11]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([C:33]#[C:32][C:30]([C:28]4[N:27]=[CH:26][O:25][CH:29]=4)([OH:34])[CH3:31])[CH:10]=3)[C:6]([CH3:18])=[N:7]2)[CH:16]=[CH:15][N:14]=1
1
C(C1=CC=CC=C1)Br.OC=1C=C(C=C(C(=O)OC)C1)C(=O)OC>C([O-])([O-])=O.[K+].[K+].CC(=O)C>COC(C1=CC(C(=O)OC)=CC(=C1)COC1=CC=CC=C1)=O
3
OC=1C=C2COC(C2=CC1O)=O>S(O)(O)(=O)=O.[N+](=O)(O)[O-]>OC=1C=C2COC(C2=C(C1O)[N+](=O)[O-])=O
3
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8](O)[C:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][N:5]=1.P(Cl)(Cl)([Cl:19])=O>>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][C:7]1[C:8]([Cl:19])=[N:9][C:4]([CH2:3][O:2][CH3:1])=[N:5][CH:6]=1)[CH3:16]
1
C1(CCCCC1)C(=O)Cl.N1C=C(C=C1)C(=O)OC>O.C(C)OCC.ClCCl.[Sn](Cl)(Cl)(Cl)Cl>C1(CCCCC1)C(=O)C1=CC(=CN1)C(=O)OC
3
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:26])[C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC=CC=2)=[CH:14][CH:13]=1.C(O)(C)C>[H][H].[C].[Pd]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:26])[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1
1
C(C)N1CCCCC1.BrC=1C=C2C(=C(N1)Br)SC=C2>>C(C)C1CCN(CC1)C=1N=C(C=C2C1SC=C2)Br
5
[CH2:1]([O:3][C:4]([C:6]1([CH2:20]I)[CH2:10][CH2:9][N:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:7]1)=[O:5])[CH3:2].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1>>[CH2:1]([O:3][C:4]([C:6]1([CH2:20][O:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:7]1)=[O:5])[CH3:2]
1
C(C)(=O)Cl.ClC(C1=NSC(=N1)N)(Cl)Cl>C1(=CC=C(C=C1)C)C.C2=C(C=CC=C2C)C.C3=CC=CC(=C3C)C>C(C)(=O)NC1=NC(=NS1)C(Cl)(Cl)Cl
3
NC1=C(C=C(C=C1)O)[N+](=O)[O-].FC1=CC=C(C=C1)C(C)=O>N(C)(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>NC1=C(C=C(C=C1)OC1=CC=C(C=C1)C(C)=O)[N+](=O)[O-]
3
ClCCCO.FCCCO>>FCCCOS(=O)(=O)C1=CC=C(C)C=C1
5
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:8]([C:18](=[O:36])[N:19]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[CH3:20])=[CH:7][N:6]=1)=[O:4].CO.O1CCOCC1.[OH-].[Na+]>O>[F:30][C:28]([F:29])([F:31])[C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=1)[CH2:21][N:19]([CH3:20])[C:18]([C:8]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1)=[O:36]
1
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:34])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]=[C:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22](=[O:29])[NH:21][C:20]4[CH:30]=[CH:31][CH:32]=[CH:33][C:19]3=4)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH2:37]([N:21]1[C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:18](=[CH:17][CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][C:9]([C:6]3[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=3)([OH:34])[CH2:10][CH2:11]2)[C:19]2[CH:33]=[CH:32][CH:31]=[CH:30][C:20]1=2)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
1
ClC=1C(=C(C(=CC1)N1N=NC(=C1)C(F)(F)F)C=1C=CC(=NC1)C(CC1=NOC=N1)N1N=CC(=C1)C1=CC(=C(C(=O)N)C=C1)F)F>O(O[H])[H].CO[H].C[Re](=O)(=O)=O>C(N)(=O)C1=C(C=C(C=C1)C=1C=NN(C1)C(CC1=NOC=N1)C1=[N+](C=C(C=C1)C1=C(C(=CC=C1N1N=NC(=C1)C(F)(F)F)Cl)F)[O-])F
3
C1(=CC=CC=C1)C1=C(NC2=CC=CC=C12)C(=O)OCC>C1CCCO1.[OH-].[Na+]>C1(=CC=CC=C1)C1=C(NC2=CC=CC=C12)C(=O)O
3
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]4[O:26][C:27](=S)[N:28]=[C:22]4[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:28][C:27]([NH:13][CH2:14][CH2:15][N:11]([CH3:12])[CH3:8])=[O:26])[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
1
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[N:10][N:11]([CH2:17][C:18]([O-:20])=O)[C:12]=2[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:33]1C=CN=C1)=O.[OH-].[NH4+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:21]3[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=3)=[N:10][N:11]([CH2:17][C:18]([NH2:33])=[O:20])[C:12]=2[C:13]([F:14])([F:16])[F:15])=[CH:6][CH:7]=1
1
[CH2:1]([O:8][C:9](=[O:27])[C@@H:10]([NH:19][C:20]([O:22]C(C)(C)C)=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(N(CC)C(C)C)(C)C.[C:44]([NH:51][C@H:52](C(O)=O)[CH3:53])([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH2:1]([O:8][C:9](=[O:27])[C@@H:10]([NH:19][C:20](=[O:22])[C@@H:52]([NH:51][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH3:53])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
2
[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[CH:14]=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19]>CCCCCC>[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1/[CH:14]=[CH:17]/[C:18]([OH:20])=[O:19])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
1
CN1N=CC(=C1)C(=O)O>ClCCl.C(C(=O)Cl)(=O)Cl>CN1N=CC(=C1)C(=O)Cl
3
C(C1=CC=CC=C1)NCC1=CC=CC=C1.O(C1=CC=CC=C1)C[C@@H]1CO1>>C(C1=CC=CC=C1)N(C[C@@H](COC1=CC=CC=C1)O)CC1=CC=CC=C1
5
CI.N1CCCC2=CC(=CC=C12)C(=O)OC>N(C)(C)C=O.O.[H-].[Na+]>CN1CCCC2=CC(=CC=C12)C(=O)OC
3
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=O)[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(=CC(=O)C[C@@H]1C)CC3>>[CH3:4][C@:3]12[CH2:21][CH2:20][C@H:19]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@:16]3([CH2:17][OH:18])[CH2:15][CH2:14][CH2:13][CH:12]=4)[C@@H:5]1[CH2:6][CH2:7][C@@H:2]2[OH:1]
1
NC1C=CC(N[C:9]2[S:10][CH:11]=[C:12]([C:14]3[S:18][C:17]([NH:19][C:20]([NH2:22])=[NH:21])=[N:16][C:15]=3[CH3:23])[N:13]=2)=CC=1.[NH2:24][C:25]1[C:26](C(=S)N)=[N:27][C:28]([Cl:32])=[C:29]([NH2:31])[N:30]=1>>[NH2:24][C:25]1[C:26]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[S:18][C:17]([NH:19][C:20]([NH2:22])=[NH:21])=[N:16][C:15]=3[CH3:23])[N:13]=2)=[N:27][C:28]([Cl:32])=[C:29]([NH2:31])[N:30]=1
2
OC=1C=C2C=CC(=CC2=CC1)C=O.FCCCOS(=O)(=O)C1=CC=C(C)C=C1>CC#N.C(=O)([O-])[O-].[Cs+].[Cs+]>FC(CC)OC=1C=C2C=CC(=CC2=CC1)C=O
3
ClCC(=O)N1CCC2=CC=CC=C12.N1CC(OCC1)CO>>OC[C@H]1OCCN(C1)CC(=O)N1CCC2=CC=CC=C12
5
[CH3:1][C:2]1[CH:3]=[C:4]([O:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)(=[O:36])=[O:35])(=[O:27])=[O:26])[CH:5]=[C:6]([CH:23]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11]C1C=CC=C2C(NC(=O)C=12)=O.C[NH2:45]>O1CCCC1.C(O)C.C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]([O:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)(=[O:36])=[O:35])(=[O:27])=[O:26])[CH:5]=[C:6]([CH:23]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11][NH2:45]
1
C(C)I.CC1=NNC2=C(C=C(C=C12)C(=O)OCC)O>>COC=1C=C(C=C2C(=NNC12)C)C(=O)OCC
5
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][C:12](=[O:28])[C:11]=1[C:29]1[NH:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[N:30]=1)[CH2:2]2.[OH-].[Na+]>Br.CC(O)=O>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@H:3]([NH:9][C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][C:12](=[O:28])[C:11]=1[C:29]1[NH:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=1)[CH2:2]2
1
ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CC=1N=CC(=NC1)NC(OC(C)(C)C)=O>ClCCl.C(=O)(C(F)(F)F)O.C(C)(=O)OCC>ClC=1C=C(C=CC1)C=1C=C(C=NC1OC)CC=1N=CC(=NC1)N
3
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].I[CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])O.[Na+]>CN(C=O)C.C1COCC1.C(OCC)(=O)C.O>[CH2:20]([NH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14])[CH2:21][CH2:22][CH3:23]
1
O[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[N:21][C:20]=2[N:26]2[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[H][H]>CO.Cl.O1CCOCC1.[Pd]>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:2][CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=3)=[CH:12][CH:13]=2)=[O:33])=[C:20]([N:26]2[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]2)[N:21]=1
2
BrCC(=O)OCC.NC1=C(C=C(C=C1)O)C>O.C([O-])([O-])=O.[K+].[K+].CC(=O)C>NC1=C(C=C(OCC(=O)OCC)C=C1)C
3
COC1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C)CC(C(=O)O)C1=CN(C2=CC=CC=C12)COCC[Si](C)(C)C>C1CCCO1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>N1C=C(C2=CC=CC=C12)C(C(=O)O)CC1=NN(C(=C1)C1=CC=C(C=C1)C)C1=CC=C(C=C1)OC
3
C(\C=C\C)=O>C(C)OCC.N1CCCCC1.C(CCCCCCCCCCC)S>C(CCCCCCCCCCC)C(C(C=O)S)C
3
[CH3:1][CH:2]1[C:11]2([CH:16]=[CH:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13][CH2:12]2)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=O>C(O)C.[Pd]>[CH3:1][C:2]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1
1
>>
5
C[Si](CCOCN1C=NC(=C1)C#N)(C)C>BrN1C(CCC1=O)=O.C(Cl)(Cl)(Cl)Cl.CC(C)(C#N)/N=N/C(C)(C)C#N>BrC=1N(C=C(N1)C#N)COCC[Si](C)(C)C
3
[Li].N.Cl.[NH:4]1[C:12]2[C:7](=[C:8]([C:13]3(O)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.O1CCCC1>C(O)C>[NH:15]1[CH2:16][CH2:17][CH2:18][CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[CH:6]=[CH:5][NH:4]3)[CH2:14]1
1
[CH:1](NC(C)C)(C)[CH3:2].[F:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.C(I)C>O1CCCC1.O>[CH2:1]([C:14]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[F:8])[CH3:2]
1
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[C:13]3[N:14]([N:18]=[C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=4)[N:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.[NH:32]1[CH2:35][CH:34](CNC(=O)OC(C)(C)C)[CH2:33]1.[CH3:45][N:46](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CN(C=O)C.ClCCl>[CH3:45][NH:46][CH:34]1[CH2:33][N:32]([C:26]([C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:19]3[N:20]=[C:13]4[C:12]([C:9]5[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH:10]=5)=[CH:17][CH:16]=[CH:15][N:14]4[N:18]=3)=[CH:30][CH:29]=2)=[O:27])[CH2:35]1
2
ClC1=CC=C(C=O)C=C1.C(C)OC(C=C(OCC)N)=O>CCO[H]>C(C)OC(=O)C1=C(N=C(C(C1C1=CC=C(C=C1)Cl)C(=O)OCC)OCC)N
3
C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(=O)O>O.C(=O)(C(F)(F)F)O>O[C@H]1C[C@H](NC1)C(=O)O
3
OCC1=CC=C(O1)C=O.OCC=1OC(=CC1)CO>>C(C)OCC=1OC(=CC1)COCC
5
Cl[C:2]1[N:3]=[C:4]([N:18]2[CH2:21][C:20]([F:23])([F:22])[CH2:19]2)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[Cl:24][C:25]1[N:29]=[CH:28][N:27]([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][C:31]=2[O:37][CH3:38])[N:26]=1.C(O)(=O)C>C1COCC1.CO>[Cl:24][C:25]1[N:29]=[CH:28][N:27]([C:30]2[CH:36]=[CH:35][C:33]([NH:34][C:2]3[N:3]=[C:4]([N:18]4[CH2:19][C:20]([F:23])([F:22])[CH2:21]4)[C:5]4[CH2:10][CH2:9][CH:8]([C:11]5[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=5)[C:6]=4[N:7]=3)=[CH:32][C:31]=2[O:37][CH3:38])[N:26]=1
1
[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH2:15])=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2.Cl[C:17]1[N:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH:15][C:17]4[N:18]=[CH:19][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=4)=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2
1
[C]=O.BrC1=C(C(=C(N)C=C1)F)C(F)F>>NC1=C(C(=C(C(=O)OC)C=C1)C(F)F)F
5
[CH2:1]([CH:8]([C:14]([NH:16][C@H:17]([C:28]1[S:29][CH:30]=[C:31]([CH2:33][CH3:34])[N:32]=1)[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:15])[C:9]([O:11]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:41](=[N:44]O)([NH2:43])[CH3:42]>C1(C)C=CC=CC=1>[CH2:33]([C:31]1[N:32]=[C:28]([C@@H:17]([NH:16][C:14](=[O:15])[CH:8]([C:9]2[O:11][N:44]=[C:41]([CH3:42])[N:43]=2)[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)[S:29][CH:30]=1)[CH3:34]
1
CN1N=NNC1=O.BrCCC1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F>CC#N.C([O-])([O-])=O.[K+].[K+]>CN1N=NN(C1=O)CCC1=CC=C(C=C1)C1=NOC(=N1)C(F)(F)F
3
Cl[C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.[NH2:11][CH:12]1[CH2:16][O:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13]1.C(N(CC)CC)C>O>[Cl:8][C:7]1[C:2]([NH:11][CH:12]2[CH2:16][O:15][CH:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[N:3][CH:4]=[N:5][C:6]=1[CH2:9][CH3:10]
1
[N+:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)([O-])=O.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38]([NH:41][C:42]([C:44]3[CH:51]=[CH:50][C:47]([CH:48]=O)=[CH:46][CH:45]=3)=[O:43])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1>>[CH3:28][N:29]1[CH2:30][CH2:31][N:32]([C:35]2[CH:36]=[CH:37][C:38]([NH:41][C:42](=[O:43])[C:44]3[CH:45]=[CH:46][C:47]([C:48]4[NH:10][C:9]5[CH:8]=[CH:7][C:6]([NH:13][C:14](=[O:27])[C:15]6[CH:20]=[CH:19][C:18]([N:21]7[CH2:26][CH2:25][O:24][CH2:23][CH2:22]7)=[CH:17][CH:16]=6)=[CH:5][C:4]=5[N:1]=4)=[CH:50][CH:51]=3)=[CH:39][CH:40]=2)[CH2:33][CH2:34]1
1
C(C)C=1NC(C(=C(N1)CCC)CC1=CC=C(C=C1)C=1C(=CC=CC1)C#N)=O.O1CCC(CC1)OC1=CC=C(C=N1)B(O)O>>C(C)C=1N(C(C(=C(N1)CCC)CC1=CC=C(C=C1)C=1C(=CC=CC1)C#N)=O)C=1C=NC(=CC1)OC1CCOCC1
5
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1.[C:16]([O:20][C:21](=[O:30])[NH:22][C@@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][OH:25])([CH3:19])([CH3:18])[CH3:17].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:16]([O:20][C:21](=[O:30])[NH:22][CH:23]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:24][O:25][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1)([CH3:19])([CH3:18])[CH3:17]
1
C([O:3][C:4]([CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][C:11]=1[CH3:12])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:3][CH2:4][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][C:11]=1[CH3:12]
1
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Reaction SMILES Dataset

A collated dataset of 3.4M unique chemical reaction SMILES strings compiled from multiple public sources for use in pre-training and fine-tuning chemical language models.

Reaction SMILES (Simplified Molecular Input Line Entry System) extend the standard SMILES notation to represent complete chemical reactions. They encode reactants, reagents/catalysts, and products in a single text string using the > delimiter:

reactants>reagents>products

For example: CC(=O)O.CCO>[H+]>CC(=O)OCC.O represents the esterification of acetic acid with ethanol to form ethyl acetate.

Dataset Features

  • smiles: The reaction SMILES string
  • source_id: Original data source identifier

Data Sources

Source ID Source URL
1 US Patents 1976-Sep2016 Grants
2 US Patents 2001-Sep2016 Applications
3 CRD 1.37M Dataset (2024)
4 USPTO Year 2023
5 Reaction SMILES Dataset (2023)

License

This dataset aggregates publicly available reaction data. Please refer to the individual source links for specific licensing terms.

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Size of downloaded dataset files:
413 MB
Size of the auto-converted Parquet files:
413 MB
Number of rows:
3,474,262