Metal free synthesis of 1‐azaspiro[4.4]nonane‐3‐one system via reactions of nitrones with 1,1‐disubstituted allenes | Zendy

Amrutha U. | Zendy; P.Babu Beneesh | Zendy; Prathapan Sreedharan | Zendy

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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.

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