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The Synthesis and Reactions of N ‐Hydroxy‐3‐Arylsydnone‐4‐Carboxamide Oximes
Author(s) -
Yeh MouYung,
Chan FatFong,
Tien HsienJu,
Fuchigami Toshio,
aka Tsutomu
Publication year - 1989
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.198900021
Subject(s) - chemistry , hydroxylamine , carboxamide , aryl , yield (engineering) , reactivity (psychology) , catalysis , medicinal chemistry , alkyl , organic chemistry , medicine , materials science , alternative medicine , pathology , metallurgy
N ‐Hydroxy‐3‐arylsydnone‐4‐carboxamide oximes (7) were prepared from the corresponding 3‐arylsydnone‐4‐carbohydroximic acid chlorides (6) and hydroxylamine in high yield. The chemical reactivity of compound (2) is somewhat different from 3‐arylsydnone‐4‐carboxamide oximes (2) in that the former compounds reacted with both aromatic and aliphatic aldehydes in the presence of acid catalyst to give 3‐aryl‐4‐(5‐aryl‐1,2,4‐oxadiazol‐3‐yl)sydnones (5) and 3‐aryl‐4‐(5‐alkyl‐1,2,4‐oxadiazol‐3‐yl)sydnones (3).