Regioselective Synthesis of 3‐Substituted Pyrroles by Nucleophilic Addition of 3‐(1‐Arylsulfonylalkyl) Pyrroles Activated under Basic or Acid Conditions | Zendy

Martinelli Fabio | Zendy; Palmieri Alessandro | Zendy; Petrini Marino | Zendy

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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.

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