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Telescoped continuous flow generation of a library of highly substituted 3-thio-1,2,4-triazoles

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Abstract

We report herein the successful application of continuous flow micro reactors to prepare important building blocks based on the 3-thio-1,2,4-triazole core. A telescoped continuous flow process was developed based on the condensation of hydrazides and isothiocyanates to deliver an in situ stream of a thiosemicarbazide, which subsequently was cyclized under basic conditions. The obtained 1,2,4-triazole-3-thiol was further alkylated with benzyl/alkyl halides. In addition, we evaluated the scope of heterocycle formation and alkylation using different hydrazides, isothiocyanates, and aryl/alkyl chlorides, bromides and iodides. We were able to synthesize a small library of 18 compounds in 48 minutes of residence time for each synthesis, and in moderate to excellent yields, in a telescoped fashion. The fully integrated synthesis flow platform enables the fast generation of compound libraries, reducing the time consumed in preliminary stages of a drug discovery process.

Graphical abstract: Telescoped continuous flow generation of a library of highly substituted 3-thio-1,2,4-triazoles

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Publication details

The article was received on 17 Aug 2017, accepted on 04 Oct 2017 and first published on 04 Oct 2017


Article type: Paper
DOI: 10.1039/C7RE00125H
Citation: React. Chem. Eng., 2017, Advance Article
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    Telescoped continuous flow generation of a library of highly substituted 3-thio-1,2,4-triazoles

    M. C. F. C. B. Damião, R. Galaverna, A. P. Kozikowski, J. Eubanks and J. C. Pastre, React. Chem. Eng., 2017, Advance Article , DOI: 10.1039/C7RE00125H

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