SMIRKS Examples

Transform descriptionSMIRKSExample Reaction
Catechol oxidation:

JOC, 1987, p5053. #50


 [O:1]([H:10])[c:2]1[cH:3][cH:4][c:5]([O:6][H:11])[cH:7][c:8]1[$(C),$(Cl),$(OC),$(CC):9]>>[O:1]=[C:2]1[CH:3]=[CH:4][C:5](=[O:6])[CH:7]=[C:8]1[$(C),$(Cl),$(OC),$(CC):9].[H:10][H:11]
 CCCc1c(O)ccc(O)c1>>CCCC1=CC(=O)C=CC1=O.[H][H]
Diels-alder:


 [C:1]=[C:2][C:3]=[C:4].[C:5]=[C:6]>>[C:1]1[C:2]=[C:3][C:4][C:5][C:6]1
 C=CC=C.C=C>>C1CCC=CC1
Alkylation:


 [*+0;n,N,S,O:1][C:2][*;Br,I:3]>>[*+1:1][C:2].[*-1:3]
 CBr.CCOCC>>CC[O+](C)CC.[Br-]
Amide formation:


 [C:1](=[O:2])Cl>>[C:1](=[O:2])N
 CCC(=O)Cl>>CCC(=O)N
Two products:


 [C:1]=[O:2]>>[H][C:1][O:2][H]
 O=CC(C)CCC=O>>CC(CCCO)C=O.CC(CO)CCC=O
Ugi:


 [C:2]1[C:3][CH:4]=[N:5][C:6]1.[N+:7]#[C-:8].[C:10](=[O:11])[O:12][H:88]>>[H:88][N:7][C:8](=[O:12])[CH:4]([C:3][C:2]1)[N:5]([C:10]=[O:11])[C:6]1
 C1CC=NC1.[C-]#[N+]CCC.c1cc(Cl)ccc1C(=O)O>>CCCNC(=O)C1CCCN1C(=O)c2ccc(Cl)cc2
Chiral inversion:


 [H:1][*@:2]([*:3])([*:4])[*:5]>>[H:1][*@@:2]([*:3])([*:4])[*:5]
 C[C@H](Cl)CCN>>C[C@@H](Cl)CCN
Nitro-group Conversion:


 [*:1][N:2](=[O:3])=[O:4]>>[*:1][N+:2](=[O:3])[O-:4]
 CN(=O)=O>>C[N+](=O)[O-]
Amide formation #2:


 [C:1](=[O:2])[Cl:3].[H:99][N:4]([H:100])[C:0]>>[C:1](=[O:2])[N:4]([H:100])[C:0].[Cl:3][H:99]
 CCCCN.CCCC(=O)Cl>>CCCCNC(=O)CCC.Cl
Swern oxidation:

JOC, 1987, p4851. #48


 [*:1][C:2]([H:3])([O:4][H:5])[C:6]([H:7])([O:8][H:9])[*:10]>>[*:1][C:2](=[O:4])[C:6](=[O:8])[*:10].[H:3][H:5].[H:7][H:9]
 C1CC(O)C(O)CC1>>O=C1CCCCC1=O.[H][H]
Diiodosilane reagant:

JOC, 1987, p4846. #49


 [*:1][CH:2]([OH:3])[*:4].[I:5][SiH2:6][I:7]>>[*:1][CH:2]([I:5])[*:4].[OH:3][SiH2:6][I:7]
 I[SiH2]I.CCCCC(O)CCC>>CCCCC(I)CCC.O[SiH2]I
EZ inversion:


 [*:0]/[C:1]([H:4])=[C:2]([H:5])/[*:3]>>[*:0]/[C:1]([H:4])=[C:2]([H:5])\[*:3]
 C=CCC/C=C/CCl>>ClC/C=C\CCC=C
Ketal formation:


 [C:1]=O>>[C:1]1OCCO1
 C1CCCCC1=O>>C1COC2(CCCCC2)O1
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