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Sydnone Compounds. XX. The Synthesis and the Schmidt Reaction of 4‐Formyl‐3‐Arylsydnone
Author(s) -
Yeh MouYung,
Tien HsienJu,
Huang LlngYuang,
Chen MengHsin
Publication year - 1983
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.198300005
Subject(s) - chemistry , sulfuric acid , sodium azide , schmidt reaction , yield (engineering) , sydnone , hydrazoic acid , oleum , reaction conditions , azide , medicinal chemistry , inorganic chemistry , organic chemistry , catalysis , ring (chemistry) , materials science , metallurgy
Abstract A convenient method to prepare 4‐formyl‐3‐arylsydone (I) from 3‐arylsydnone by the Vilsmeier reaction in moderate yields (30%‐76%) was carefully investigated. According to the Schmidt reaction, I reacts with sodium azide in concentrated sulfuric acid to produce 3‐arylsydnone‐4‐carboxamide (II). But 3‐arylsydnone‐4‐carhonitrile (III) is obtained, if dilute sulfuric acid was used instead. When III treates with concentrated sulfuric acid, II is obtained in good yield. The all possible reaction mechanisms are suggested.