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Synthesis 2019; 51(19): 3600-3610
DOI: 10.1055/s-0037-1611854
DOI: 10.1055/s-0037-1611854
paper
PhI(OAc)2-Mediated Regioselective Synthesis of 5-Guanidino-1,2,4-thiadiazoles and 1,2,4-Triazolo[1,5-a]pyridines via Oxidative N–S and N–N Bond Formation
The authors thank the SERB, New Delhi, India for financial support in the form of NPDF (PDF/2016/000177).Further Information
Publication History
Received: 15 February 2019
Accepted after revision: 24 April 2019
Publication Date:
08 July 2019 (online)
Abstract
An effective and expeditious approach for the construction of biologically important 5-guanidino-1,2,4-thiadiazole and 1,2,4-triazolo[1,5-a]pyridine derivatives has been developed. This new protocol involves the phenyliodine(III) diacetate [PhI(OAc)2]-mediated oxidative cyclization of thioureas/2-aminopyridines and imidates via N–S and N–N bond formation at ambient temperature. This method furnishes the versatile 5-guanidino-1,2,4-thiadiazoles and 1,2,4-triazolo[1,5-a]pyridines in a scalable manner with high efficiency and excellent regioselectivity.
Key words
metal-free - regioselectivity - high efficiency - wide substrate scope - insensitivity to air and moisture - 5-guanidino-1,2,4-thiadiazoles - 1,2,4-triazolo[1,5-a]pyridines - gram scaleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611854.
- Supporting Information
- CIF File
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For selected reviews on hypervalent iodine reagents, see:
For examples of C–C bond forming heterocycles using hypervalent iodine(III) reagents, see:
For examples of C–X (X = N, O, S) bond forming heterocycles using hypervalent iodine(III) reagents, see:
For examples of N–X (X = N, O, S) bond forming heterocycles using hypervalent iodine(III) reagents, see: