Direct Construction of the 9H‐Pyrrolo[1, 2‐a]azepin‐9‐amine Skeleton via [4+3] Annulation of Alkyl 2‐Aroyl‐1‐chlorocyclo‐ propanecarboxylates. Issue 13 (14th September 2015)

• Record Type: Journal Article
• Authors: Hu, Junhao; Liu, Yang; Gong, Yuefa
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 13(2015)
• Page Start: 2781
• Page End: 2787
• Publication Date: 2015-09-14
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500376
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A direct diastereoselective synthesis approach of important 9<italic>H</italic>‐pyrrolo[1, 2‐<italic>a</italic>]azepin‐9‐amines was established <italic>via</italic> base‐promoted [4+3] annulation between donor–acceptor reagents derived from 1<italic>H</italic>‐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 &gt;20:1).</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj2n0t61b6" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>