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Preprint Communication Version 1 Preserved in Portico This version is not peer-reviewed

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

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.

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

CHEMISTRY, Organic Chemistry

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

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