Example Transformations:

Reaction:

[CH3:1][C:17]([CH3:2])([CH3:3])[c:16]1[cH:12][cH:10][c:15]
([CH2:4][Mg]Br)[cH:11][cH:13]1.[cH:5]1[cH:6][cH:8][n:14]
[cH:9][cH:7]1>CCOC(=O)Cl.[Cu]I.O=O.C1CCOC1>[CH3:1][C:17]
([CH3:2])([CH3:3])[c:16]1[cH:12][cH:10][c:15]([CH2:4]
[c:5]2[cH:6][cH:8][n:14][cH:9][cH:7]2)[cH:11][cH:13]1

Transform:

[H:1][c:7]1[c:3][c:5][n:8][c:6][c:4]1.[C:2][Mg]Br>>
[H+:1].[C:2][c:7]1[c:3][c:5][n:8][c:6][c:4]1

Notes: The aromatic pyridine ring is included in the transform. Also, the sole explicit hydrogen is the pyridyl hydrogen which is replaced during the reaction. All other valences are unspecified.


Reaction:

[CH3:1][O:7][c:15]1[cH:9][cH:8][c:13]2[N:11]([CH3:2])
[C:12](=O)[C@@:16]([CH3:3])([CH2:6][CH2:5][NH2:4])[c:14]2
[cH:10]1>>[CH3:1][O:7][c:15]1[cH:9][cH:8][c:13]2
[N:11]([CH3:2])[C@H:12]3[N:4](C)[CH2:5][CH2:6]
[C@@:16]3([CH3:3])[c:14]2[cH:10]1

Transform:

[H+:1].[N:2]([H:3])[H:4].[C:5]=O>>
[H+:3].[H+:4].[H:1][C:5][N:2]C

Notes: The fact that this is an intra-molecular reaction is not reflected in the transform. Also, steric effects of a rigid substrate aren't reflected.


Reaction:

[CH3:1][O:6]/[CH:9]=[CH:10]/[CH:7]=[CH2:3].[CH3:2][C:11]
(=[CH2:4])[CH:8]=[O:5]>>[CH3:1][O:6][C@@H:9]1[CH:10]=[CH:7]
[CH2:3][CH2:4][C@:11]1([CH3:2])[CH:8]=[O:5]

Transform:

[C:1]=[C:5][C:6]=[C:2].[C:3]=[C:7][C:8]=[O:4]>>
[O:4]=[C:8][C:7]1[C:3][C:1][C:5]=[C:6][C:2]1

Notes: We must show the obligatory Diels-Alder... The carbonyl (directly conjugated to the reacting center) is kept. The methoxyl isn't. The transform doesn't capture knowledge of the regio-specificity of the reaction; the anti isomer forms, it is just less favored. Also note that the stereochemical information is lost (the transform SMILES throws away the stereo during its global stereochemical analysis).


Reaction:

[CH3:1][C:17](=[O:3])[CH:16]1[CH2:12][CH2:8][CH2:5]
[CH2:9][CH2:13]1.[O:2]=[CH:14][CH:15]1[CH2:10][CH2:6]
[CH2:4][CH2:7][CH2:11]1>>C[CH:14]([OH:2])[CH:15]1[CH2:10]
[CH2:6][CH2:4][CH2:7][CH2:11]1.C[C:17]([CH3:1])([OH:3])
[CH:16]1[CH2:12][CH2:8][CH2:5][CH2:9][CH2:13]1

Transform:

Before Splitting:
[H+:1].[H+:2].[C:3]=[O:5].[C:4]=[O:6]>>
[H:1][O:5][C:3]C.[H:2][O:6][C:4]C

#1
[H+:1].[C:3]=[O:5]>>[H:1][O:5][C:3]C

#2
[H+:2].[C:4]=[O:6]>>[H:2][O:6][C:4]C

Notes: In this case, the reaction actually captures two independent transformations. After identifying the transforms from the overall reaction, the components are split out to yield two independent transformations. In this case the two transformations are identical after canonicalization, which renumbers the atoms maps.

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