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Nitrosation of methyl 2‐acylamino‐3‐dimethylaminopropenoates. A simple conversion of n ‐acylglycines into 5‐substituted 1,2,4‐Oxadiazole‐3‐carboxylates
Author(s) -
Kmetiĉ Matej,
Stanovnik Branko
Publication year - 1995
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.5570320525
Subject(s) - chemistry , oxadiazole , nitrosation , phosphorus , simple (philosophy) , medicinal chemistry , organic chemistry , combinatorial chemistry , epistemology , philosophy
A novel simple synthesis of 5‐substituted‐1,2,4‐oxadiazole‐3‐carboxylates 5 from N ‐acylglycines 1 , which are transformed with DMF in the presence of phosphorus oxychloride into 2‐substituted‐4‐dimethyl‐aminomethyleneoxazol‐5(4 H )‐ones 2 , followed by opening into 2‐aroylamino‐3‐dimethylamino‐propenoates 3 , and nitrosation to give the oximes 4 as intermediates, which cyclize spontaneously into 5‐substituted‐1,2,4‐oxadiazole‐3‐carboxylates 5 . The compounds 2 can be transformed into 5 without isolation of 3 and 4 .