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Lewis Acid‐Catalyzed Synthesis of Functionalized Pyrroles
Author(s) -
Attanasi Orazio A.,
Berretta Stefano,
De Crescentini Lucia,
Favi Gianfranco,
Giorgi Gianluca,
Mantellini Fabio
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800807
Subject(s) - chemistry , lewis acids and bases , catalysis , lewis acid catalysis , ring (chemistry) , brønsted–lowry acid–base theory , michael reaction , sequence (biology) , combinatorial chemistry , organic chemistry , biochemistry
The synthesis of highly functionalized pyrroles is described. The sequence involves the preliminary preparation of α‐aminohydrazones by Michael addition of primary amines to 1,2‐diaza‐1,3‐butadienes. The treatment of these compounds with dialkyl acetylenedicarboxylates produces α‐( N ‐enamino)‐hydrazones that were converted into the corresponding pyrroles by Lewis acid‐catalyzed ring closure. A screening of several Lewis/Brønsted acid catalysts was also performed.