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Easy One‐Pot Synthesis of Fused Heterocycles from 1,2‐Diaza‐1,3‐dienes
Author(s) -
Attanasi Orazio A.,
Bianchi Luca,
De Crescentini Lucia,
Favi Gianfranco,
Mantellini Fabio
Publication year - 2011
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.201100340
Subject(s) - chemistry , pyrrole , pyridine , sequence (biology) , stereochemistry , medicinal chemistry , organic chemistry , biochemistry
Abstract A base‐promoted chemoselective synthesis of 6a‐hydroxy‐6,6a‐dihydro‐1 H ‐thieno[3,4‐ b ]pyrrole‐3,3a(4 H )‐dicarboxylates, 5‐(2‐furylmethyl)‐6a‐hydroxy‐6‐oxo‐4,5,6,6a‐tetrahydropyrrolo[3,4‐ b ]pyrrole‐3,3a(1 H )‐dicarboxylates, and 5‐benzyl‐7a‐hydroxy‐1,4,5,6,7,7a‐hexahydro‐3a H ‐pyrrolo[3,2‐ c ]pyridine‐3,3a‐dicarboxylates starting from diazadienes and heterocycles containing an activated methine group has been developed. This transformations proceeds by Michael addition/5‐ exo cyclization sequence.