Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmet...

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Main Authors:	Zhengning Ma, Zicheng Ma, Dawei Zhang
Format:	Article
Language:	English
Published:	MDPI AG 2018-10-01
Series:	Molecules
Subjects:	pyrrole heterocycles TosMICs electron-deficient compounds Van Leusen pyrrole synthesis [3+2] cycloaddition
Online Access:	http://www.mdpi.com/1420-3049/23/10/2666

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record_format	Article
spelling	doaj-3b1ae1000811413c976109f6ecfc5d532020-11-24T21:23:14ZengMDPI AGMolecules1420-30492018-10-012310266610.3390/molecules23102666molecules23102666Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient CompoundsZhengning Ma0Zicheng Ma1Dawei Zhang2College of Chemistry, Jilin University, Changchun 130012, ChinaCollege of Chemistry, Jilin University, Changchun 130012, ChinaCollege of Chemistry, Jilin University, Changchun 130012, ChinaPyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.http://www.mdpi.com/1420-3049/23/10/2666pyrrole heterocyclesTosMICselectron-deficient compoundsVan Leusen pyrrole synthesis[3+2] cycloaddition
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Zhengning Ma Zicheng Ma Dawei Zhang
spellingShingle	Zhengning Ma Zicheng Ma Dawei Zhang Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds Molecules pyrrole heterocycles TosMICs electron-deficient compounds Van Leusen pyrrole synthesis [3+2] cycloaddition
author_facet	Zhengning Ma Zicheng Ma Dawei Zhang
author_sort	Zhengning Ma
title	Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds
title_short	Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds
title_full	Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds
title_fullStr	Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds
title_full_unstemmed	Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds
title_sort	synthesis of multi-substituted pyrrole derivatives through [3+2] cycloaddition with tosylmethyl isocyanides (tosmics) and electron-deficient compounds
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2018-10-01
description	Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.
topic	pyrrole heterocycles TosMICs electron-deficient compounds Van Leusen pyrrole synthesis [3+2] cycloaddition
url	http://www.mdpi.com/1420-3049/23/10/2666
work_keys_str_mv	AT zhengningma synthesisofmultisubstitutedpyrrolederivativesthrough32cycloadditionwithtosylmethylisocyanidestosmicsandelectrondeficientcompounds AT zichengma synthesisofmultisubstitutedpyrrolederivativesthrough32cycloadditionwithtosylmethylisocyanidestosmicsandelectrondeficientcompounds AT daweizhang synthesisofmultisubstitutedpyrrolederivativesthrough32cycloadditionwithtosylmethylisocyanidestosmicsandelectrondeficientcompounds
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Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

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