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

✍ Scribed by Kazuhiro Kobayashi; Seiki Fujita; Daisuke Nakai; Shogo Fukumoto; Shuhei Fukamachi; Hisatoshi Konishi

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 168 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000172

✦ Synopsis

Abstract

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.