Sequential MCR via Staudinger/Aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-Amino-1H-Imidazole-2(3H)-Thiones

8Citations
Citations of this article
8Readers
Mendeley users who have this article in their library.

Abstract

A multicomponent reaction (MCR) strategy, alternative to the known cycloaddition reaction, towards variously substituted 1-amino-1H-imidazole-2(3H)-thione derivatives has been successfully developed. The novel approach involves α-halohydrazones whose azidation process followed by tandem Staudinger/aza-Wittig reaction with CS2 in a sequential MCR regioselectively leads to the target compounds avoiding the formation of the regioisomer iminothiazoline heterocycle. The approach can be applied to a range of differently substituted α-halohydrazones bearing also electron-withdrawing groups confirming the wide scope and the substituent tolerance of the process for the synthesis of the target compounds. Interestingly, the concurrent presence of reactive functionalities in the scaffolds so obtained ensures post-modifications in view of N-bridgeheaded heterobicyclic structures.

References Powered by Scopus

Recent developments in isocyanide based multicomponent reactions in applied chemistry

4326Citations
N/AReaders
Get full text

Chemistry and biology of multicomponent reactions

2295Citations
N/AReaders
Get full text

The aza-Wittig reaction: an efficient tool for the construction of carbon-nitrogen double bonds

391Citations
N/AReaders
Get full text

Cited by Powered by Scopus

An electrochemical oxidative multicomponent cascade annulation of ketones and amines used to produce imidazoles

45Citations
N/AReaders
Get full text

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

12Citations
N/AReaders
Get full text

In situ generation of imines by the Staudinger/aza-Wittig tandem reaction combined with thermally induced Wolff rearrangement for one-pot three-component β-lactam synthesis

8Citations
N/AReaders
Get full text

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Cite

CITATION STYLE

APA

Ciccolini, C., Mari, G., Favi, G., Mantellini, F., de Crescentini, L., & Santeusanio, S. (2019). Sequential MCR via Staudinger/Aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-Amino-1H-Imidazole-2(3H)-Thiones. Molecules, 24(20). https://doi.org/10.3390/molecules24203785

Readers' Seniority

Tooltip

PhD / Post grad / Masters / Doc 2

67%

Professor / Associate Prof. 1

33%

Readers' Discipline

Tooltip

Chemistry 4

80%

Psychology 1

20%

Save time finding and organizing research with Mendeley

Sign up for free