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

Kobayashi Kazuhiro | Zendy; Matsumoto Kota | Zendy; Nakamura Daizo | Zendy; Fukamachi Shuhei | Zendy; Konishi Hisatoshi | Zendy

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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.

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