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Metal free synthesis of 1‐azaspiro[4.4]nonane‐3‐one system via reactions of nitrones with 1,1‐disubstituted allenes
Author(s) -
Amrutha U.,
P.Babu Beneesh,
Prathapan Sreedharan
Publication year - 2019
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.3718
Subject(s) - chemistry , fluorenone , fluorene , nonane , pyrrolidine , cycloaddition , aryl , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , polymer , alkyl
In the cycloaddition reaction between fluorenone N ‐aryl nitrones and 1,1‐disubstituted allenes, the initially formed cycloadduct underwent facile [1,3] shift to give 1′‐phenylspiro[fluorene‐9,2′‐pyrrolidin]‐4′‐ones. Although 1′‐phenylspiro[fluorene‐9,2′‐pyrrolidin]‐4′‐ones are stable in solid state, a few of them underwent facile aerial oxidation in solution to give the corresponding 1′‐phenylspiro[fluorene‐9,2′‐pyrrolidine]‐4′,5′‐diones in excellent overall yields.