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

Tumula Nagaraju; Palakodety Radha Krishna; Balasubramanian Sridhar; Nakka Mangarao

doi:10.1055/s-0037-1611854

Synthesis, Table of Contents

Synthesis 2019; 51(19): 3600-3610
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

Tumula Nagaraju

^aOrganic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Email: mangarao@csiriict.in

^bAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India

,

Palakodety Radha Krishna ∗

^aOrganic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Email: mangarao@csiriict.in

,

Balasubramanian Sridhar

^cCenter for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

,

Nakka Mangarao∗

^aOrganic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Email: mangarao@csiriict.in

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Abstract

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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 scale

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References

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