Issue 13, 2022

Migratory cycloisomerization of 1,3-dien-5-ynes conjugated with pseudopeptides in assembly of benzo[7]annulenes

Abstract

A novel domino cycloisomerization of 1,3-dien-5-ynes for the synthesis of 7H-benzo[7]annulenes is reported. The noticeable feature of this domino reaction involves the assembly of the fused bicyclic motifs through a transamidation/5-exo-trig cyclization/8π-electrocyclization sequence in a single step. Finally, mechanistic investigations were conducted experimentally and supported by DFT calculations.

Graphical abstract: Migratory cycloisomerization of 1,3-dien-5-ynes conjugated with pseudopeptides in assembly of benzo[7]annulenes

Supplementary files

Article information

Article type
Communication
Submitted
20 Nov 2021
Accepted
17 Jan 2022
First published
17 Jan 2022

Chem. Commun., 2022,58, 2164-2167

Migratory cycloisomerization of 1,3-dien-5-ynes conjugated with pseudopeptides in assembly of benzo[7]annulenes

H. Khosravi, H. J. Ghazvini, M. Kamangar, F. Rominger and S. Balalaie, Chem. Commun., 2022, 58, 2164 DOI: 10.1039/D1CC06533E

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