Hydriodic Acid‐Mediated Cyclization of  α ‐Substituted Secondary 2‐Ethenylbenzamides: Synthesis of 2‐Substituted 2,3‐Dihydro‐3,3‐dimethyl‐1 H ‐isoindol‐1‐ones and 3,3‐Disubstituted ( E )‐1‐(Arylimino)‐1,3‐dihydroisobenzofurans | Zendy

Kobayashi Kazuhiro | Zendy; Fujita Seiki | Zendy; Nakai Daisuke | Zendy; Fukumoto Shogo | Zendy; Fukamachi Shuhei | Zendy; Konishi Hisatoshi | Zendy

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Hydriodic Acid‐Mediated Cyclization of α ‐Substituted Secondary 2‐Ethenylbenzamides: Synthesis of 2‐Substituted 2,3‐Dihydro‐3,3‐dimethyl‐1 H ‐isoindol‐1‐ones and 3,3‐Disubstituted ( E )‐1‐(Arylimino)‐1,3‐dihydroisobenzofurans

Author(s) -

Kobayashi Kazuhiro,

Fujita Seiki,

Nakai Daisuke,

Fukumoto Shogo,

Fukamachi Shuhei,

Konishi Hisatoshi

Publication year - 2010

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201000172

Subject(s) - chemistry , benzamide , aryl , alkyl , medicinal chemistry , stereochemistry , organic chemistry

A new and facile method for the preparation of 2‐substituted 2,3‐dihydro‐3,3‐dimethyl‐1 H ‐isoindol‐1‐ones 3 and 3,3‐disubstituted ( E )‐1‐(arylimino)‐1,3‐dihydroisobenzofurans 6 has been developed. Thus, treatment of N ‐alkyl(or aryl)‐2‐(1‐methylethen‐1‐yl)benzamides 2 with concentrated hydriodic acid (HI) in MeCN at room temperature afforded 3 . Similar treatment of N ‐aryl‐2‐(1‐phenylethen‐1‐yl)benzamide 5 with concentrated HI at 0° afforded 6 .

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