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A Convenient Synthesis of 2,3‐Dihydro‐3‐methylidene‐1 H ‐isoindol‐1‐ones by Reaction of 2‐Formylbenzonitriles with Dimethyloxosulfonium Methylide
Author(s) -
Kobayashi Kazuhiro,
Matsumoto Kota,
Nakamura Daizo,
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.201000035
Subject(s) - chemistry , substituent , yield (engineering) , iodide , medicinal chemistry , methyl iodide , stereochemistry , organic chemistry , materials science , metallurgy
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.