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Vol. 29 No. 9 (2017): Vol 29 Issue 9

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A Facile Synthesis of Amide Derivatives of [1,2,4]Triazolo[4,3-a]pyridine

https://doi.org/10.14233/ajchem.2017.20624
N. Murthy Gandikota
Department of Chemistry, K.L. University, Green Fields, Vaddeswaram, Guntur-522 502, India
R. Sekhar Bolla
Department of Chemistry, K.L. University, Green Fields, Vaddeswaram, Guntur-522 502, India
I.V. Kasi Viswanath
Department of Chemistry, K.L. University, Green Fields, Vaddeswaram, Guntur-522 502, India
Sridharreddy Bethi
G.V.K. Bio Sciences, Hyderabad, India

Corresponding Author(s) : I.V. Kasi Viswanath

viswanath_fed@kluniversity.in

Asian Journal of Chemistry, Vol. 29 No. 9 (2017): Vol 29 Issue 9

Abstract

A facile synthesis for preparation of amide derivatives of [1,2,4]triazolo[4,3-a]pyridine can be achieved by the nucleophilic displacement of chloromethyl derivative with methyl amine followed by the reaction with acid analogues in the presence of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU). Reaction of 2-chloropyridine with hydrazine hydrate (99 %) gave 2-hydrazinopyridine (2). Compound 3 was obtained in good yields by treating 2-hydrazinopyridine with chloroacetyl chloride. Further 3-chloromethyl-[1,2,4]triazolo[4,3-a]pyridine (4) is obtained by treatment of compound 3 with POCl3. Nucleophilic displacement of compound 4 with methyl amine gave methyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl-amine (5). Finally protecting and deprotecting of compound 5 with Boc anhydride and HCl in dioxane gives hydrochloride salt of compound 5 i.e. (6) The reaction of hydrochloride salt of methyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl-amine with 10 different acids yields amide analogues.

Keywords

s-Triazolo pyridines Pyridine derivatives 1,2,4-Triazolo[4,3-a]pyridine Triazolo derivatives
Gandikota, N. M., Bolla, R. S., Viswanath, I. K., & Bethi, S. (2017). A Facile Synthesis of Amide Derivatives of [1,2,4]Triazolo[4,3-a]pyridine. Asian Journal of Chemistry, 29(9), 1920–1924. https://doi.org/10.14233/ajchem.2017.20624
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