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

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

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 multicomponen...

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Main Authors: Hassan Farhid, Mohammad Mahdi Rostami, Ahmad Shaabani, Behrouz Notash
Format: Article
Language:English
Published: Georg Thieme Verlag KG 2021-06-01
Series:SynOpen
Subjects:
depsipeptide
passerini reaction
isocyanide
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/a-1533-3823
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spelling doaj-f9d3cf0b2f284c3b90da64157a3575cd2021-07-07T23:05:02ZengGeorg Thieme Verlag KGSynOpen2509-93962021-06-01050316717210.1055/a-1533-3823Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent ReactionsHassan Farhid0Mohammad Mahdi Rostami1Ahmad Shaabani2Behrouz Notash3Faculty of Chemistry, Shahid Beheshti UniversityFaculty of Chemistry, Shahid Beheshti UniversityFaculty of Chemistry, Shahid Beheshti UniversityDepartment of Inorganic Chemistry and Catalysis, Shahid Beheshti UniversityAn 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.http://www.thieme-connect.de/DOI/DOI?10.1055/a-1533-3823depsipeptidepasserini reactionisocyanide
collection DOAJ
language English
format Article
sources DOAJ
author Hassan Farhid
Mohammad Mahdi Rostami
Ahmad Shaabani
Behrouz Notash
spellingShingle Hassan Farhid
Mohammad Mahdi Rostami
Ahmad Shaabani
Behrouz Notash
Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions
SynOpen
depsipeptide
passerini reaction
isocyanide
author_facet Hassan Farhid
Mohammad Mahdi Rostami
Ahmad Shaabani
Behrouz Notash
author_sort Hassan Farhid
title Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions
title_short Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions
title_full Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions
title_fullStr Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions
title_full_unstemmed Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions
title_sort synthesis of depsipeptides via isocyanide-based consecutive bargellini–passerini multicomponent reactions
publisher Georg Thieme Verlag KG
series SynOpen
issn 2509-9396
publishDate 2021-06-01
description 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.
topic depsipeptide
passerini reaction
isocyanide
url http://www.thieme-connect.de/DOI/DOI?10.1055/a-1533-3823
work_keys_str_mv AT hassanfarhid synthesisofdepsipeptidesviaisocyanidebasedconsecutivebargellinipasserinimulticomponentreactions
AT mohammadmahdirostami synthesisofdepsipeptidesviaisocyanidebasedconsecutivebargellinipasserinimulticomponentreactions
AT ahmadshaabani synthesisofdepsipeptidesviaisocyanidebasedconsecutivebargellinipasserinimulticomponentreactions
AT behrouznotash synthesisofdepsipeptidesviaisocyanidebasedconsecutivebargellinipasserinimulticomponentreactions
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