M. Kaur, Baldev Singh, Baljit Singh
Nov 1, 2013
Citations
0
Influential Citations
4
Citations
Journal
Journal of Chemical Sciences
Abstract
Abstract1,3-Dipolar cycloaddition of nitrilimines 3 with N-benzyl maleimide 4 has provided 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives 5 in excellent yield as the only isomer through a concerted pathway. Graphical AbstractNitrilimines have been prepared in situ by base catalysed dehydrohalogenation of hydrazonyl halides. Their cycloaddition with N-benzyl maleimides having carbon–carbon double bond has been carried out which leads to the synthesis of 5-benzyl-1-(2′,4′-dibromophenyl)-3-(4″-substituted phenyl)-3a,4,6,6atetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives as the single isomer. Stereochemical studies revealed that addition follows cis-endo addition rule.