Ultrasound‐promoted 1,3‐dipolar cycloaddition of azomethine yields for synthesis of dispiropyrrolidineoxindole derivatives in hexyltriphenylphosphonium bromide as an ionic liquid, and the evaluation of their anti‐cancer activity

A green, effortless, and protective one‐pot three‐component process for the synthesis of derivatives using cycloadition catching azomethineylides in situ created by means of decarboxylative build‐up of sarcosine and isatin has been developed in hexyltriphenylphosphonium bromide (HTPB) as an ionic li...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 60; no. 3; pp. 416 - 422
Main Authors Matloubi Moghaddam, Firouz, Hosseinzadeh, Nouraddin, Safari, Fatemeh, Foroumadi, Alireza
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Inc 01.03.2023
Wiley
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Subjects
Anticancer properties
Chemistry
Chemistry, Organic
Cycloaddition
Ionic liquids
Physical Sciences
Science & Technology
Stereoselectivity
Synthesis
CANCER-CELLS
CATALYSIS
ONE-POT SYNTHESIS
REGIOSELECTIVE SYNTHESIS
EFFICIENT SYNTHESIS
ANTIBACTERIAL
ISATIN DERIVATIVES
INHIBITORS
TRANSFORMATIONS
ALKALOIDS
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Summary:A green, effortless, and protective one‐pot three‐component process for the synthesis of derivatives using cycloadition catching azomethineylides in situ created by means of decarboxylative build‐up of sarcosine and isatin has been developed in hexyltriphenylphosphonium bromide (HTPB) as an ionic liquid and recyclable solvent in supreme yield without the use of a catalyst under ultrasonic irradiation. This method offers mild reaction conditions, excellent products yields in shorter reaction times, ease of operation and environmentally friendly process and high ragio and stereoselectivity. The anticancer activity of all new compounds has been investigated against four cell lines. Also, the structures were authenticated by both spectroscopic techniques and signal crystal X‐ray analysis.
Bibliography:Funding information
Sharif University of Technology
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4595