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Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo‐Condensed 1,3‐Oxazines
Author(s) -
Petina Olga A.,
Yakovlev Igor P.,
Geffken Detlef
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200267
Subject(s) - chemistry , oxazines , chloride , thermal decomposition , medicinal chemistry , decomposition , organic chemistry
Abstract Reaction of phenylpropynehydrazide with dimethylmalonyl chloride furnished the corresponding 4,4‐dimethyl‐1‐(3‐phenylprop‐2‐ynoyl)pyrazolidine‐3,5‐dione, which upon thermolysis underwent a 6‐ endo ‐ dig cyclization to a pyrazolo[5,1‐ b ][1,3]oxazine. The corresponding reaction of arylpropynehydrazides with monosubstituted malonyl chlorides furnished pyrazolo[5,1‐ b ][1,3]oxazine‐7‐ones via intermediates that could not be isolated.