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Reactions with Naphthoylhydroxlmoyl Chlorides: Synthesis of Derivatives of Isoxazole, Pyrrolidino[3,4‐ d ]isoxazoiin‐4,6‐dione, lmidazo[1,2‐a]pyridine, lmidazo[1,2‐a]pyrimidine, Benzotriazine and Benzothiadiazine
Author(s) -
Abdelhamid Abdou O.,
AlHamidi Abdulaziz A.
Publication year - 1995
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199500014
Subject(s) - chemistry , sodium ethoxide , isoxazole , pyridine , yield (engineering) , medicinal chemistry , benzothiadiazine , acrylonitrile , pyrimidine , phenylisocyanate , organic chemistry , stereochemistry , ethanol , materials science , copolymer , metallurgy , polymer
Hydroximoyl chlorides 3 react with acrylonitrile, N ‐arylmaleimide and maleic anhydride to give isoxazolines 5 , pyrrolidino[3,4‐ d ]isoxazolines 8 , and furolidino[3,4‐ d ]isoxazolines 9 , respectively. 3 reacted with 2‐aminopyridine, 2‐aminopyrimidine, o ‐phenylenediamine and o ‐aminothiophenol to yield 3‐ni‐trosoimidazo[1,2‐α]pyridines 20 , 3‐nitrosopyrimidines 22 , 3‐naphthoyl‐1,4‐dihydrobenzo‐1,2,4‐triazines 24 , and 3‐naphthoyl‐4 H ‐1,3,4‐benzothiadiazine 27 , respectively. Compound 3 reacted with benzoylacetonitrile, acetoacetanilide, thiophenol, benzencsulfinic acid in ethanolic sodium ethoxide solution to give the corresponding isoxazoles 12–13 and oximes 16–17 , respectively. The structures of these products were confirmed by elemental analyses, spectral data and, wherever possible, alternative synthesis.