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Synthesis of New Piperidine based N(2)-Alkylated 1,2,3-Triazole Hybrids in Basic Medium
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 az...
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Published in: | Asian journal of chemistry 2023-01, Vol.35 (1), p.212-216 |
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Main Authors: | , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites |
Online Access: | Get full text |
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Summary: | 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). |
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ISSN: | 0970-7077 0975-427X |
DOI: | 10.14233/ajchem.2023.26906 |