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A Convenient Synthesis of 2,3-Dihydro-3-methylidene-1H-isoindol-1-ones by Reaction of 2-Formylbenzo­nitriles with Dimethyloxosulfonium Methylide

✍ Scribed by Kazuhiro Kobayashi; Kota Matsumoto; Daizo Nakamura; Shuhei Fukamachi; Hisatoshi Konishi

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
137 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A facile method for the synthesis of 2,3‐dihydro‐3‐methylidene‐1__H__‐isoindol‐1‐one and its derivatives carrying substituent(s) at C(5) and/or C(6) has been developed. The reaction of 2‐formylbenzonitrile (1a) with dimethyloxosulfonium methylide, generated by the treatment of trimethylsulfoxonium iodide with NaH in DMSO/THF at 0°, resulted in the formation of 2,3‐dihydro‐3‐methylidene‐1__H__‐isoindol‐1‐one (2a) in 77% yield. Similarly, six 2‐formylbenzonitriles carrying substituent(s) at C(4) and/or C(5), i.e., 1b–1g, also gave the corresponding expected products 2b–2g in comparable yields.

📜 SIMILAR VOLUMES

Synthesis of 2-Aryl-2,3-dihydro-3-sulfan
Synthesis of 2-Aryl-2,3-dihydro-3-sulfanyl-1H-isoindol-1-ones by Pummerer-Type Cyclization of N-Aryl-2-(sulfinylmethyl)benzamides
✍ Kazuhiro Kobayashi; Hiroo Hashimoto; Teruhiko Suzuki; Hisatoshi Konishi 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 German ⚖ 162 KB

## Abstract An efficient method for the synthesis of 2‐aryl‐2,3‐dihydro‐3‐sulfanyl‐1__H__‐isoindol‐1‐ones **1** __via Pummerer__‐type cyclization of __N__‐aryl‐2‐(sulfinylmethyl)benzamides **2** is described. Thus, treatment of these sulfinyl‐benzamides **2**, easily prepared from 2‐(bromomethyl)be