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Convenient synthesis of 3‐arylazopyrazoles and 2‐arylazo‐1,3,4‐Δ 2 ‐ thiadiazoline derivatives from 3‐nitroformazans
Author(s) -
Abdelhamid Abdou O.,
Abbas Ikhlass M.,
Abdallah Magda A.,
Fahmi Abdelgawad A.,
Shawali Ahmad S.
Publication year - 1985
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.5570220340
Subject(s) - chemistry , malononitrile , acetylacetone , acetanilide , potassium thiocyanate , dibenzoylmethane , nitro , medicinal chemistry , carbanion , thiourea , thiocyanate , reagent , organic chemistry , alkyl , catalysis
Reactions of 3‐nitro‐1,5‐diarylformazans 1a‐c with carbanions of acetylacetone, dibenzoylmethane, aceto‐acetanilide, benzoylacetonitrile, ω‐benzenesulfonylacetophenone and malononitrile yielded the corresponding 3‐arylazopyrazole derivatives 4‐9 respectively. Reactions of 1 with nucleophiles result in displacement of the nitro group and the formation of the corresponding 3‐substituted formazans 10‐13 . Treatment of 1 with potassium thiocyanate gave, however, 5‐imino‐2‐arylazo‐1,3,4‐Δ 2 ‐thiadiazolines 14. Structural assignments have been made on the basis of spectral and elemental analyses, chemical behaviour and alternate synthesis wherever possible.