Preprint Communication Version 1 This version is not peer-reviewed

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Version 1 : Received: 25 September 2019 / Approved: 26 September 2019 / Online: 26 September 2019 (09:46:54 CEST)

A peer-reviewed article of this Preprint also exists.

Ciccolini, C.; Mari, G.; Favi, G.; Mantellini, F.; De Crescentini, L.; Santeusanio, S. Sequential MCR via Staudinger/Aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-Amino-1H-Imidazole-2(3H)-Thiones. Molecules 2019, 24, 3785. Ciccolini, C.; Mari, G.; Favi, G.; Mantellini, F.; De Crescentini, L.; Santeusanio, S. Sequential MCR via Staudinger/Aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-Amino-1H-Imidazole-2(3H)-Thiones. Molecules 2019, 24, 3785.

Journal reference: Molecules 2019, 24, 3785
DOI: 10.3390/molecules24203785

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 postmodifications in view of N-bridgedheaded heterobicyclic structures.

Subject Areas

multicomponent reaction; α-halohydrazones; staudinger reaction; aza-wittig; 1h-imidazole-2(3h)-thione; 2h-imidazo[2,1-b][1,3,4]thiadiazine

Comments (0)

We encourage comments and feedback from a broad range of readers. See criteria for comments and our diversity statement.

Leave a public comment
Send a private comment to the author(s)
Views 0
Downloads 0
Comments 0
Metrics 0


×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.