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A simple and facile synthesis of novel 1,2,3‐triazole substituted pyrimidine derivatives
Author(s) -
Bakkolla Mahesh Goud,
Taduri Ashok Kumar,
Bhoomireddy Rama Devi
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.3964
Subject(s) - chemistry , cycloaddition , click chemistry , indole test , dimethylformamide , yield (engineering) , ethyl cyanoacetate , guanidine , triazole , pyrimidine , ethanol , 1,2,3 triazole , hydrochloride , combinatorial chemistry , propargyl bromide , organic chemistry , malononitrile , stereochemistry , catalysis , solvent , materials science , metallurgy
A series of novel indole and pyrimidine scaffolds bearing 1,2,3‐triazoles have been designed and synthesized using click chemistry reaction conditions. Target compounds 9a‐j were synthesized in the multi‐step process. In the first step 5‐substituted‐1‐methyl‐1 H ‐indole‐3‐carbaldehyde 2a‐b reacted with ethyl cyanoacetate 3 and guanidine hydrochloride 4 in presence of L‐Proline in ethanol undergoes cyclisation to form 5a‐b . Further, 5a‐b condensed with various benzaldehydes to form Schiff's base 6a‐f , which further proporgylated with propargyl bromide to form 7a‐f . Finally, 7a‐f was subjected to click‐chemistry with various azides in the presence of CuSO 4 .5H 2 O + sodium ascorbate mixture in Dimethylformamide at room temperature to obtain 2 + 3 cycloaddition products 9a‐j in high yield. All these synthetic methods are mostly green and inexpensive with excellent yields.