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Synthesis of New Spirooxindole‐Fused Isoxazoline/Triazole and Isoxazoline/Isoxazole Derivatives from Three‐Component 1,3‐Dipolar Cycloaddition
Author(s) -
Sakly Randa,
Edziri Hayet,
Askri Moheddine,
Knorr Michael,
Louven Kathrin,
Strohmann Carsten,
Mastouri Maha
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.2981
Subject(s) - isoxazole , chemistry , cycloaddition , regioselectivity , propargyl , 1,3 dipolar cycloaddition , catalysis , triazole , component (thermodynamics) , stereochemistry , combinatorial chemistry , organic chemistry , physics , thermodynamics
A series of diverse heterocycles containing spirooxindole, isoxazoline/triazole, and isoxazole rings has been synthesized via an efficient three‐component reaction of ( E )‐2‐(1‐propargyl‐2‐oxoindoline‐3‐ylidene)acetophenones 1 , arylnitrile oxides 2 , and arylazides 3 using Cu(I) as catalyst. The regiochemistry and stereochemistry of cycloadducts 4a and 5a have been confirmed by X‐ray diffraction studies. The heterocycles were screened against Gram‐positive and Gram‐negative bacteria and fungi. Several compounds exhibit moderate to excellent activities comparable to those of established standard drugs.