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Article

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

Department of Biomolecular Sciences, Section of Chemistry and Pharmaceutical Technologies, University of Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino (PU), Italy
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Academic Editor: Wim Dehaen
Molecules 2019, 24(20), 3785; https://doi.org/10.3390/molecules24203785
Received: 25 September 2019 / Revised: 11 October 2019 / Accepted: 15 October 2019 / Published: 21 October 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
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. View Full-Text
Keywords: multicomponent reaction; α-halohydrazones; Staudinger reaction; aza-Wittig; 1H-imidazole-2(3H)-thione; 2H-imidazo[2,1-b][1,3,4]thiadiazine multicomponent reaction; α-halohydrazones; Staudinger reaction; aza-Wittig; 1H-imidazole-2(3H)-thione; 2H-imidazo[2,1-b][1,3,4]thiadiazine
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MDPI and ACS Style

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. https://doi.org/10.3390/molecules24203785

AMA Style

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(20):3785. https://doi.org/10.3390/molecules24203785

Chicago/Turabian Style

Ciccolini, Cecilia, Giacomo Mari, Gianfranco Favi, Fabio Mantellini, Lucia De Crescentini, and Stefania Santeusanio. 2019. "Sequential MCR via Staudinger/Aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-Amino-1H-Imidazole-2(3H)-Thiones" Molecules 24, no. 20: 3785. https://doi.org/10.3390/molecules24203785

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