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Copper‐catalyzed Synthesis of N ‐alkylated 2‐(4‐substituted‐1 H ‐1,2,3‐triazol‐1‐yl)‐1 H ‐indole‐3‐carbaldehyde by Step‐wise and One‐pot Three‐component Huisgen's 1,3‐dipolar Cycloaddition Reaction
Author(s) -
Avula Vijay Kumar Reddy,
Vallela Swetha,
Anireddy Jaya Shree,
Chamarthi Naga Raju
Publication year - 2017
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.2918
Subject(s) - chemistry , cycloaddition , indole test , catalysis , alkylation , 1,3 dipolar cycloaddition , oxindole , halide , medicinal chemistry , solvent , combinatorial chemistry , organic chemistry
An efficient method for the synthesis of N ‐alkylated 2‐(4‐substituted‐1 H ‐1,2,3‐triazol‐1‐yl)‐1 H ‐indole‐3‐carbaldehyde has been developed starting from oxindole and indole using Huisgen's 1,3‐dipolar cycloaddition reaction of organic azides to alkynes. The effect of catalysts and solvent on these reactions has been investigated. Among all these conditions, while using CuSO 4 ·5H 2 O, DMF was found to be the best system for this reaction. It could also be prepared in a one‐pot three‐component manner by treating equimolar quantities of halides, azides, and alkynes. The Huisgen's 1,3‐dipolar cycloaddition reaction was performed using CuSO 4 ·5H 2 O in DMF with easy work‐up procedure.