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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 .