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Cycloaddition Reactions of 3‐Methyloxazolium‐5‐olates to 4‐Arylidene‐5(4 H )‐isoxazolones
Author(s) -
Clerici Francesca,
Erba Emanuela,
Mornatti Pierluigi,
Trimarco Pasqualina
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891220215
Subject(s) - chemistry , cycloaddition , nonane , pyrrole , medicinal chemistry , reaction conditions , organic chemistry , stereochemistry , catalysis
The unstable cycloadducts formed from benzylideneisoxazolones 2 and oxazolium‐5‐olates 1 undergo CO 2 elimination to afford the stereoisomeric substituted 3,7‐diazaspiro[4,4]nonane derivatives 3 , which were isolated in one case ( 3a , b ). On further reaction, compounds 3 are transformed into pyrrole‐3‐carboxylic acids 4 . Reaction paths and regiochemical behaviour are discussed.