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Paper | Regular issue | Vol 27, No. 3, 1988, pp.695-706
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4381
Chemistry of C-Heteroarylhydrazidoyl Halides. Synthesis and Reactions of N-(p-Nitrophenyl)-C-(2-thienyl)-formohydrazidoyl Halides

Hamdi M. Hassaneen,* Hiyam A. H. Mousa, Nosrat M. Abed, and Ahmad S. Shawali

*Girls College, Science Department, General Presidency for Girls Education, Riyadh, Saudi Arabia

Abstract

Synthesis of C-(2-thienyl)-N-(p-nitrophenyl)formohydrazidoyl chloride 5a and its bromide analog 5b is described. Both 5a and 5b react with oxygen, sulfur and nitrogen nucleophiles in ethanol to give the corresponding substitution products 7-9. The cycloadditions of the nitrilimine 10, generated in situ from 5, to various olefinic dipolarophiles have been carried out. All reactions studied proceed with complete regioselectivity to give the 2-pyrazoline derivatives 11-13 and 16. Moreover, cycloaddition of 10 with enolates of various active methylene compounds afforded the pyrazole derivatives 22 and 27 in high yields. The cycloaddition regioselectivity is discussed in terms of the frontier orbital method.