ChemInform Abstract: QUINAZOLINE DERIVATIVES WITH PHYTOEFFECTOR OR BIOCIDAL PROPERTIES

Suesse, M.; Johne, S.

doi:10.1002/chin.198215354

Cited by 1 publication

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“…It is concluded that reactions of the aminobenzothiophene and aminopyranopyrazole carbonitrile derivatives with substituted benzylidenemalononitriles proceed by attack of the amino group at one of the two cyano groups and not at the -carbon of the unsaturated system. 7,13 On the other hand, in their reactions with acetylenic esters and ketones, attack of the amino group at the -carbon of the acetylenic system [14][15][16] takes place, rather than at the carbonyl function.…”

Section: Discussionmentioning

confidence: 99%

Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones

Youssef

2009

Journal of Chemical Research

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Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile (1a) with substituted benzylidenemalononitriles gave 4-amino-2-(1-cyano-2-arylvinyl)benzothieno[2,3- d]pyrimidine derivatives (3) as ( E,Z)-mixtures and in one case (2c) as separated ( Z)- and ( E)-isomers. Similar treatment of 6-amino-1,4-dihydro-3-methyl-1,4-diphenyl-pyrano[2,3- c]pyrazole-5-carbonitrile (4) yielded similarly-formed pyrazolopyranopyrimidine derivatives (5a, b) as ( Z)-and ( E)-stereoisomers. Attempted acetylation of the aminobenzothienopyrimidines resulted in degradation of the pyrimidine ring and the formation of N-(3-cyano-4,5,6,7-tetrahydro[1]benzothien-2-yl)acetamide (1b). Treatment of 4 with acetylenic esters and ketones (6a-d) afforded the ( Z)-substituted enaminopyrano[2,3- c]pyrazole derivatives. Reacting 1a with aroyl phenyl acetylenes gave by Michael addition the enamino-ketones (8a-c).

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Section: Discussionmentioning

confidence: 99%

Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones

Youssef

2009

Journal of Chemical Research

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ChemInform Abstract: QUINAZOLINE DERIVATIVES WITH PHYTOEFFECTOR OR BIOCIDAL PROPERTIES

Cited by 1 publication

References 0 publications

Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones

Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones

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