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Regioselective Synthesis of 3‐Substituted Pyrroles by Nucleophilic Addition of 3‐(1‐Arylsulfonylalkyl) Pyrroles Activated under Basic or Acid Conditions
Author(s) -
Martinelli Fabio,
Palmieri Alessandro,
Petrini Marino
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100434
Subject(s) - regioselectivity , nucleophile , reagent , electrophile , chemistry , sulfonyl , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , alkyl
Conditioned pyrroles! Sulfonyl pyrroles, obtained regioselectively from commercial N ‐triisopropylsilylpyrrole, undergo removal of the arylsulfonyl group under basic or acidic conditions to give vinylogous imino‐like derivatives (see scheme; TIPS=triisopropylsilyl). These electrophilic intermediates react with nucleophilic reagents to give 3‐functionalized pyrroles.