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Vol. 35 No. 1 (2023): Vol 35 Issue 1

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Synthesis of New Piperidine based N(2)-Alkylated 1,2,3-Triazole Hybrids in Basic Medium

https://doi.org/10.14233/ajchem.2023.26906
Venkata Ramana Murthy Appala
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500085, India ; Chemveda Life Sciences Pvt Ltd., IDA Uppal, Hyderabad-500039, India
Kanaka Durga Bhavani Anagani
Department of Chemistry, Osmania University, Hyderabad-500007, India ; Department of Chemistry, Avanthi Degree and P.G. College (Affiliated to OsmaniaUniversity), Himayath Nager, Hyderabad-500029, India
Aparna Pasula
Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, College of Engineering, Kukatpally, Hyderabad-500085, India

Corresponding Author(s) : Venkata Ramana Murthy Appala

Asian Journal of Chemistry, Vol. 35 No. 1 (2023): Vol 35 Issue 1

Abstract

The nucleophilic reaction of 1H-triazole derivatives with piperidines under basic conditions is the essential step in the synthesis of a new series of dibenzyl N(2)-C-linked triazolyl piperidines. The triazole derivative was synthesized via the CuAAc reaction of 1-phenylprop-2-yn-1-ol (1a-b) with azidomethyl pivalate. Compound 3a-b underwent dehydroxylation and deprotection reactions using TFA, triethyl silane and 1 M NaOH respectively, yielding monobenzyl 1H-1,2,3-triazole (4a-b). The N(2)-piperidinyltriazoles (6a-j) were synthesized in significant amounts by nucleophilically reacting 1H-triazole derivatives (4a-b) with 4-mesyl-1-boc-piperidine (5) under basic conditions using sodium hydride, which further on acidic deprotection followed by benzylation reaction furnished dibenzyl N(2)-C-linked triazolyl piperidines (9a-j).

Keywords

Click reaction Propynol Azidomethyl pivalate 4-Mesyl-1-boc-piperidine Sodium hydride Piperidinyl triazole
Ramana Murthy Appala, V., Durga Bhavani Anagani, K., & Pasula, A. (2022). Synthesis of New Piperidine based N(2)-Alkylated 1,2,3-Triazole Hybrids in Basic Medium. Asian Journal of Chemistry, 35(1), 212–216. https://doi.org/10.14233/ajchem.2023.26906
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