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One-Step Synthesis of Dialkyl 2-[(4-Methylphenyl)sulfonyl]-1H-pyrrole-3,4-dicarboxylates by Reaction of Acetylenedicarboxylates with ‘Tosylmethyl Isocyanide’ (TsMIC) and Triphenylphosphine

✍ Scribed by Abdolali Alizadeh; Hassan Masrouri; Sadegh Rostamnia; Farnaz Movahedi

Publisher: John Wiley and Sons
Year: 2006
Tongue: German
Weight: 61 KB
Volume: 89
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200690095

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✦ Synopsis

Abstract

The reactive 1 : 1 adducts in the reaction between Ph~3~P and dialkyl acetylenedicarboxylates have been trapped with ‘tosylmethyl isocyanide’ (TsMIC; 1) to yield dialkyl 2‐[(4‐methylphenyl)sulfonyl]‐1__H__‐pyrrole‐3,4‐dicarboxylates 3 (Scheme 1). The structures of the highly functionalized compounds 3 were corroborated spectroscopically (IR, ^1^H‐ and ^13^C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 2).

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