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Direct Construction of the 9 H ‐Pyrrolo[1,2‐ a ]azepin‐9‐amine Skeleton via [4+3] Annulation of Alkyl 2‐Aroyl‐1‐chlorocyclo‐ propanecarboxylates
Author(s) -
Hu Junhao,
Liu Yang,
Gong Yuefa
Publication year - 2015
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.201500376
Subject(s) - chemistry , annulation , alkyl , azepine , domino , reagent , amine gas treating , pyrrole , medicinal chemistry , acceptor , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , physics , condensed matter physics
A direct diastereoselective synthesis approach of important 9 H ‐pyrrolo[1,2‐ a ]azepin‐9‐amines was established via base‐promoted [4+3] annulation between donor–acceptor reagents derived from 1 H ‐pyrrole‐2‐carbaldehydes and alkyl 2‐aroyl‐1‐chlorocyclopropanecarboxylates. This transition metal‐free domino reaction proceeded quickly under mild basic conditions, affording potentially bioactive azepine derivatives in moderate to high yields with high diastereoselectivities (up to >20:1).