TBAB‐Mediated Radical 5 ‐exo‐trig ipso ‐Cyclization of 2‐Arylbenzamide for the Synthesis of Spiro[cyclohexane‐1,1′‐isoindoline]‐2,5‐diene‐3′,4‐dione | Zendy

Qiu Guanyinsheng | Zendy; Chen ZhiFeng | Zendy; Xie Wenlin | Zendy; Zhou Hongwei | Zendy

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TBAB‐Mediated Radical 5 ‐exo‐trig ipso ‐Cyclization of 2‐Arylbenzamide for the Synthesis of Spiro[cyclohexane‐1,1′‐isoindoline]‐2,5‐diene‐3′,4‐dione

Author(s) -

Qiu Guanyinsheng,

Chen ZhiFeng,

Xie Wenlin,

Zhou Hongwei

Publication year - 2019

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.201900321

Subject(s) - chemistry , isoindoline , aromatization , cyclohexane , aryl , diene , radical , halogenation , radical cyclization , aryl radical , medicinal chemistry , stereochemistry , organic chemistry , catalysis , natural rubber , alkyl

A TBAB‐mediated radical 5‐ exo‐trig ipso‐ cyclization of N ‐aryl‐2‐arylbenzamide is described herein for the synthesis of spiro[cyclohexane‐1,1′‐isoindoline]‐2,5‐diene‐3′,4‐dione. The transformation proceeds regioselectively and provides the final products with high efficiency and a broad reaction scope. Mechanism studies show the use of TBAB as an additive is pivotal for the reaction. In the process, para ‐bromination of N ‐aryl group, 5‐ exo‐tri ipso ‐cyclization of N ‐aryl‐2‐arylbenzamide nitrogen radical and sequential aromatization is involved.

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