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Stereoselective ring closure of 6‐[[(methylamino)carbonyl]oxy]‐2 H ‐pyran‐3(6 H )‐ones. Formation of the 5 H ‐pyrano[3,2‐ d ]oxazole‐2,6‐dione ring system
Author(s) -
Georgiadis Minas P.,
Couladouros Elias A.
Publication year - 1990
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.5570270646
Subject(s) - oxazole , chemistry , pyran , ring (chemistry) , stereospecificity , stereoselectivity , closure (psychology) , stereochemistry , keto–enol tautomerism , medicinal chemistry , tautomer , organic chemistry , catalysis , economics , market economy
The stereospecific formation of the 5 H ‐pyrano[3,2‐ d ]oxazole‐2,6‐dione ring system from 2,2‐disubstituted‐6‐[[(methylamino)carbonyl]oxy]‐2 H ‐pyran‐3(6 H )‐one via an enolization at C‐5 is presented. The outcome of the same reaction in the case of 2‐monosubstituted 2 H ‐pyran‐3(6 H )‐ones is also discussed.