CC BY-NC-ND 4.0 · SynOpen 2021; 05(03): 167-172
DOI: 10.1055/a-1533-3823
paper
Virtual Collection in Honor of Prof. Issa Yavari

Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions

Hassan Farhid
a  Faculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran
,
Mohammad Mahdi Rostami
a  Faculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran
,
a  Faculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran
b  Рeoples’ Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
,
Behrouz Notash
c  Department of Inorganic Chemistry and Catalysis, Shahid Beheshti University, Evin, Tehran, Iran
› Author Affiliations
This work has been supported by the Research Council of Shahid Beheshti University and the RUDN University Strategic Academic Leadership Program (A. Shaabani).


Abstract

An efficient and straightforward approach has been established for the preparation of a new class of depsipeptide structures via isocyanide-based consecutive Bargellini–Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were obtained via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via a Passerini multicomponent-reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes. The depsipeptides thus prepared have more flexible structures than their pseudopeptidic analogues.

Supporting Information



Publication History

Received: 18 May 2021

Accepted after revision: 18 June 2021

Publication Date:
22 June 2021 (online)

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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