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Paper | Regular issue | Vol 31, No. 2, 1990, pp.247-253
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5045
Synthesis and Cycloaddition Reaction of N-Phenyl-C-styrylmethanohydrazonyl Bromide

Hamidi M. Hassaneen,* Ahmad S. Shawali, and Nehal M. Elwan

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt

Abstract

N-Phenyl-C-styrylnitrilimine 4 reacts with arylidenesulphonylacetonitriles 5a-c or arylidenemalononitriles 6a-c to give exclusively 5-cyanopyrazoles 9a-c. On the other hand cylcoaddition of ethyl arylidenecyanoacetate 11a,c, α-cyanoarylideneacetophenones 12b-d and benzylidene α-cyanoacetanilide 13a with 4 yields 2-pyrazoline derivatives 14a,c, 15b-d, and 16a, respectively. Also, nitrilimine 4 reacts with N-arylmaleimides 18a-d to give the corresponding pyrrolopyrazoles 19a-d.