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Issue 6, 2017
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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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Article information


Submitted
17 Aug 2017
Accepted
04 Oct 2017
First published
04 Oct 2017

React. Chem. Eng., 2017,2, 896-907
Article type
Paper

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, 2, 896
DOI: 10.1039/C7RE00125H

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