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

Cecilia Ciccolini; Giacomo Mari; Gianfranco Favi; Fabio Mantellini; Lucia De Crescentini; Stefania Santeusanio

doi:10.20944/preprints201909.0294.v1

Preprint Communication Version 1 This version is not peer-reviewed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

Cecilia Ciccolini ,

Giacomo Mari ,

Gianfranco Favi ^* ,

Fabio Mantellini ,

Lucia De Crescentini ,

Stefania Santeusanio ^*

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

How to cite: 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. Preprints 2019, 2019090294 (doi: 10.20944/preprints201909.0294.v1). 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. Preprints 2019, 2019090294 (doi: 10.20944/preprints201909.0294.v1).

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

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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