Design, Synthesis and Characterization of N-(7-((Substituted-1H-1,2,3-triazol-5-yl) methoxy)-5-methyl-1,8-naphthyridin-2-yl) acetamide Scaffolds

Abstract

Herein, N-(7-chloro-5-methyl-1,8-naphthyridin-2-yl) acetamide (1) with Pd₂dba₃/Bippyphos catalytic amount, CsOH·H₂O, and THF to give N-(7-hydroxy-5-methyl-1,8-naphthyridin-2-yl) acetamide (2). It is treated with propargyl bromide, K₂CO₃/DMF under reflux to yield N-(5-methyl-7-(prop-2-yn-1-yloxy)-1,8-naphthyridin-2-yl) acetamide (3) viz O- propargylation. Now compound 3 is reacted with NaN₃,TEA, various substituted benzyl bromides (4a-o)  with sodium ascorbate,CuSO₄.5H₂O namely Sharpless catalyst to give desired  N-(7-((Substituted-1H-1,2,3-triazol-5-yl)methoxy)-5-methyl-1,8-naphthyridin-2-yl)acetamides  (5a-o) with promising yields as shown in  Scheme I and Fig:4. The structures of the products further confirmed by spectral  analysis.