Issue 15, 2021

Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization

Abstract

A novel and efficient method for the construction of 1,5-methanobenzo[f][1,3]oxazocin-6-one compounds from o-vinyl benzaldehydes and N-acylarylimines has been developed. The synthesis proceeded through the sequential NHC-catalyzed azabenzoin reaction and radical-initiated regioselective intramolecular cascade cyclizations. This protocol features mild conditions, good functional group tolerance and high yields of products. Novel 6,10-methanopyrido[3,2-f][1,3]oxazocin-5-ones could also be synthesized from 2-vinylnicotinaldehyde and N-acylarylimines based on this method. Capitalizing on the operational simplicity and use of efficient C–C and C–X bond-forming reactions, this protocol combining NHC-catalyzed and radical-initiated reactions enables the assembly of bridged aromatic ring-fused oxazocine derivatives with versatile functional and structural diversities.

Graphical abstract: Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization

Supplementary files

Article information

Article type
Research Article
Submitted
29 mrt 2021
Accepted
27 mei 2021
First published
02 jun 2021

Org. Chem. Front., 2021,8, 4192-4201

Construction of novel bridged aromatic ring-fused oxazocine frameworks via an N-heterocyclic carbene-catalyzed azabenzoin reaction and radical-initiated cascade cyclization

S. Niu and Y. Cheng, Org. Chem. Front., 2021, 8, 4192 DOI: 10.1039/D1QO00483B

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