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Synthesis of quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts

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Abstract

The reaction of dihydroimidazole-2-thiol with N-(3-chloro-2-oxopropyl)phthalimide gave 2-[3-(4,5-dihydroimidazol-2-ylsulfanyl)-2-oxopropyl]-1,3-dioxo-1H-isoindole which underwent intramolecular heterocyclization to dihydroimidazothiazole system by the action of a dehydrating agent. Treatment of 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazole with concentrated hydrochloric acid led to the formation of dihydroimidazo[2,1-b]thiazol-3-ylmethanamine. Water-soluble quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts were obtained by alkylation of 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazole with alkyl halides.

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Authors and Affiliations

  1. Bashkir State Medical University, ul. Lenina 3, Ufa, 450000, Bashkortostan, Russia

    V. M. Dianov

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  1. V. M. Dianov
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Original Russian Text © V.M. Dianov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 1046–1048.

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Dianov, V.M. Synthesis of quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts. Russ J Org Chem 42, 1028–1030 (2006). https://doi.org/10.1134/S1070428006070165

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  • DOI: https://doi.org/10.1134/S1070428006070165

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