Transformations of 4-arylpyrrolo[1,2-a][1,4]benzodiazepines in three-component reactions with activated alkynes and CH, NH, SH, and OH acids

Three-component reactions of tetrahydropyrrolo[1,2-a][1,4]benzodiazepines with methyl propiolate or acetylacetylene and CH, NH, SH, and OH acids were studied in various solvents. The reaction direction is assumed to depend on the nucleophilicity of anion, formed through deprotonation of acid by the anionic center of initial Michael-type zwitterion. © 2015 Springer Science+Business Media New York

Transformation of 4-substituted tetrahydro-pyrrolobenzodiazepines in a three-component reaction with methyl propiolate and indole

The three-component reaction of 4-phenyl-, p-methoxyphenyl-, and thienylpyrrolo[1,2-a][1,4]benzo-diazepines with methyl propiolate and indole in dichloromethane proceeds through opening of the diazepine ring. The major transformation products isolated are substituted pyrroles, namely, 1-(2-aminomethylphenyl)-5-(arylmethyl)-2-(indol-1(3)-yl)pyrroles and 1-(2-aminomethylphenyl)-2-aryl-(indol-3-yl)-methylpyrroles. © 2014 Springer Science+Business Media New York

Transformations of 4-arylpyrrolo[1,2-a][1,4]benzodiazepines in three-component reactions with activated alkynes and CH, NH, SH, and OH acids

Three-component reactions of tetrahydropyrrolo[1,2-a][1,4]benzodiazepines with methyl propiolate or acetylacetylene and CH, NH, SH, and OH acids were studied in various solvents. The reaction direction is assumed to depend on the nucleophilicity of anion, formed through deprotonation of acid by the anionic center of initial Michael-type zwitterion. © 2015 Springer Science+Business Media New York

Transformation of 4-substituted tetrahydro-pyrrolobenzodiazepines in a three-component reaction with methyl propiolate and indole

The three-component reaction of 4-phenyl-, p-methoxyphenyl-, and thienylpyrrolo[1,2-a][1,4]benzo-diazepines with methyl propiolate and indole in dichloromethane proceeds through opening of the diazepine ring. The major transformation products isolated are substituted pyrroles, namely, 1-(2-aminomethylphenyl)-5-(arylmethyl)-2-(indol-1(3)-yl)pyrroles and 1-(2-aminomethylphenyl)-2-aryl-(indol-3-yl)-methylpyrroles. © 2014 Springer Science+Business Media New York