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

Hassan Farhid; Mohammad Mahdi Rostami; Ahmad Shaabani; Behrouz Notash

doi:10.1055/a-1533-3823

SynOpen, Table of Contents

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

^aFaculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran

,

Mohammad Mahdi Rostami

^aFaculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran

,

Ahmad Shaabani ∗

^aFaculty of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran

^bРeoples’ Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya Street, Moscow, 117198, Russian Federation

,

Behrouz Notash

^cDepartment of Inorganic Chemistry and Catalysis, Shahid Beheshti University, Evin, Tehran, Iran

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Abstract

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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.

Key words

depsipeptide - Passerini reaction - isocyanide

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References

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