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Direct nitration of aldehyde arylhydrazones and the use of the products in the synthesis of some heterocyclic compounds
Author(s) -
Shawali Ahmad S.,
Hassaneen Hamdi M.,
Sherif Sherif M.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170822
Subject(s) - chemistry , nitration , potassium thiocyanate , acrylonitrile , benzaldehyde , methylene , aldehyde , organic chemistry , carbanion , nucleophile , medicinal chemistry , pyrazole , catalysis , polymer , copolymer
Direct nitration of substituted benzaldehyde p ‐nitrophenylhydrazones 1 gave α‐nitroarylidene‐ p ‐nitrophenylhydrazines 2 . Reactions of 2 with nucleophiles result in displacement of the nitrite. Treatment of 2 with potassium thiocyanate gave 5‐imino‐1,3,4‐Δ 2 ‐thiadiazolines 10 . Reactions of 2 with carbanions of active methylene compounds yielded the pyrazole derivatives 15–20 . 1,3‐Dipolar cycloadditions of 2 onto acrylonitrile and benzalacetophenone afforded the expected cycloadducts 21 and 22 , respectively.