Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo‐Condensed 1,3‐Oxazines | Zendy

Petina Olga A. | Zendy; Yakovlev Igor P. | Zendy; Geffken Detlef | Zendy

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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

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.

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