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Regioselective [1N+2C+2C] Assembly of Fully Decorated Pyrroles from Primary Amines, 1,2‐Diaza‐1,3‐dienes, and 2,3‐Allenoates
Author(s) -
Perrulli Francesca R.,
Favi Gianfranco,
De Crescentini Lucia,
Attanasi Orazio A.,
Santeusanio Stefania,
Mantellini Fabio
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501017
Subject(s) - hydroamination , regioselectivity , chemistry , enamine , annulation , primary (astronomy) , combinatorial chemistry , amine gas treating , tandem , organic chemistry , catalysis , physics , materials science , astronomy , composite material
A mild, sequential multicomponent reaction strategy for the regioselective synthesis of functionalized pentasubstituted pyrroles from readily accessible primary amines, 1,2‐diaza‐1,3‐dienes, and 2,3‐allenoates, has been developed. The process allows a [1N+2C+2C] annulation to be achieved through two sequential hydroamination reactions followed by an enamine‐carbocyclization. Moreover, allenoates, as synthetic equivalents of monoactived alkynes, permit the specific preparation of multifunctionalized pyrroles.