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Design and the synthesis of 1‐heteroaryl ‐1,2,3‐triazoles connected to coumarins via ether linker
Author(s) -
Nibin Joy Muthipeedika,
Beliaev Nikolai,
Beryozkina Tetyana V.,
Bakulev Vasiliy A.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4025
Subject(s) - chemistry , coumarin , linker , cycloaddition , combinatorial chemistry , click chemistry , ether , conjugate , pyrimidine , triazole , conjugated system , molecule , catalysis , stereochemistry , organic chemistry , mathematical analysis , mathematics , computer science , operating system , polymer
In this paper, we report an efficient and versatile methodology for the synthesis of a series of novel heteroaryl‐1,2,3‐triazoles connected to 4‐methylcoumarin (4‐methyl‐2H‐chromen‐2‐one) via oxymethylene linker. The desired molecules were accessed by both two‐step synthesis and the one‐pot copper catalyzed cycloaddition reaction of heteroaromatic azides with coumarin containing acetylenes. The developed protocol was found to be facile and effective for preparing a series of novel heteroaryl‐1,2,3‐triazole‐coumarin conjugates in excellent yields. Practical utility of one‐pot protocol has been confirmed by the successful gram‐scale synthesis of 1,3‐Dimethyl‐6‐(4‐[([4‐methyl‐2‐oxo‐2H‐chromen‐7‐yl]oxy)methyl]‐1H‐1,2,3‐triazol‐1‐yl)pyrimidine‐2,4(1H,3H)‐dione.