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A Facile Synthesis of Novel ( Z )‐ethyl‐3‐(5‐substituted‐1‐alkyl/aryl‐1 H ‐indol‐3‐yl)‐2‐( 1 H ‐tetrazol‐5‐yl)acrylate
Author(s) -
Bakkolla Mahesh Goud,
Taduri Ashok Kumar,
Bhoomireddy Rama Devi
Publication year - 2019
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.3375
Subject(s) - chemistry , sodium azide , tetrazole , knoevenagel condensation , aryl , alkyl , ethanol , azide , pharmacophore , combinatorial chemistry , indole test , medicinal chemistry , catalysis , organic chemistry , stereochemistry
A novel route was developed for synthesis of high potential 1 H ‐tetrazoles by using conventional method. Tetrazole scaffold is a promising pharmacophore fragment, frequently used in the development of various novel drugs. Here, the novel ( Z )‐3‐( N ‐alkyl‐indol‐3‐yl)‐2‐(1 H ‐tetrazole‐5‐yl)acrylates 5 ( a – i ) have been synthesized from ( Z )‐ethyl‐3‐(1 H ‐indol‐3‐yl)2‐(1 H ‐tetrazol‐5‐yl)acrylates 4 ( a – c ) by using various alkylating agents such as Dimethyl Sulphate (DMS), Diethyl Sulphate (DES), and benzyl chloride; 4 ( a – c ) were synthesized from sodium azide in the presence of copper sulfate in dimethylformamide; 3 ( a – c ) have been prepared by Knoevenagel condensation of indole‐3‐carbaldehyde 1 ( a – c ) and ethylcyanoacetate 2 in the presence of L‐Proline as a catalyst at room temperature in ethanol for an hour. This is an efficient and clean click chemistry method that has various advantages such as easy workup, higher yields, shorter reaction times, and more economical.