Preprint Communication Version 1 Preserved in Portico This version is not peer-reviewed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
* ORCID logo ,
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)

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.

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.

Keywords

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

Subject

Chemistry and Materials Science, Organic Chemistry

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.

Download PDF Download Supplementary

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)
* All users must log in before leaving a comment
Views 0
Downloads 0
Comments 0
Metrics 0
Get PDF Supplementary Files Cite Share 0
Bookmark BibSonomy Mendeley Reddit Delicious
×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.
We use cookies on our website to ensure you get the best experience.
Read more about our cookies here.