1H-Indazole-5,6-diamine → 6-thienyl-1H-pyrazolo[3,4-g]quinoxaline

HRID 2260108

Reaction equation

HRID 2260108 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][N:6]=[CH:5]2.[C:12]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH:13]=O>>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:12]1[CH:13]=[N:11][C:10]2[CH:9]=[C:8]3[NH:7][N:6]=[CH:5][C:4]3=[CH:3][C:2]=2[N:1]=1.[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:12]1[CH:13]=[N:1][C:2]2[CH:3]=[C:4]3[CH:5]=[N:6][NH:7][C:8]3=[CH:9][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 819001H-Indazole-5,6-diamineHCID 5272214Oxo(thiophen-2-yl)acetaldehyde

Product 2

HCID 189997996-thienyl-1H-pyrazolo[3,4-g]quinoxalineHCID 189998077-thienyl-1H-pyrazolo[3,4-g]quinoxaline

Procedure

Condensation as shown in Step A of 5,6-diaminoindazole with a glyoxyloylthiophene in the presence of absolute alcohol results in ring formation of a mixture of 6-thienyl-1H-pyrazolo[3,4-g]quinoxaline and 7-thienyl-1H-pyrazolo[3,4-g]quinoxaline. These positional isomers can be separated by standard procedures, such as column chromatography.

Workup

  1. customCondensation

Sources & evidence

ORD record
ord-ff16d6430b4b4a79a0159c115bd9bafd
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Linked notes

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