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One‐Step Synthesis of Dialkyl 2‐[(4‐Methylphenyl)sulfonyl]‐1 H ‐pyrrole‐3,4‐dicarboxylates by Reaction of Acetylenedicarboxylates with ‘Tosylmethyl Isocyanide’ (TsMIC) and Triphenylphosphine
Author(s) -
Alizadeh Abdolali,
Masrouri Hassan,
Rostamnia Sadegh,
Movahedi Farnaz
Publication year - 2006
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.200690095
Subject(s) - chemistry , sulfonyl , adduct , isocyanide , medicinal chemistry , pyrrole , proton nmr , stereochemistry , organic chemistry , alkyl
The reactive 1 : 1 adducts in the reaction between Ph 3 P and dialkyl acetylenedicarboxylates have been trapped with ‘tosylmethyl isocyanide’ (Ts MIC ; 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 ).