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 | Zendy

Hu Junhao | Zendy; Liu Yang | Zendy; Gong Yuefa | Zendy

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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).

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