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

Hormoz Khosravi; Helya Janatian Ghazvini; Mohammad Kamangar; Frank Rominger; Saeed Balalaie

doi:10.1039/D1CC06533E

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

Hormoz Khosravi,

^a Helya Janatian Ghazvini,‡^a Mohammad Kamangar,

^a Frank Rominger^b and Saeed Balalaie

*^a

Author affiliations

* Corresponding authors

^a Peptide Chemistry Research Institute, Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran
E-mail: balalaie@kntu.ac.ir

^b Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany

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.

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DOI: https://doi.org/10.1039/D1CC06533E
Article type: Communication
Submitted: 20 Nov 2021
Accepted: 17 Jan 2022
First published: 17 Jan 2022

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

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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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Chemical Communications

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

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

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