L-proline catalyzed multicomponent domino reaction in polyethyleneglycol-400 for regioselective synthesis of pyrazolyl-tetrahydroindazolones under microwave irradiation

A simple and convenient approach for the synthesis of pyrazolyl-tetrahydroindazolones via L-proline catalyzed three component domino reaction of arylhydrazine, dimedone and pyrazole aldehyde in polyethyleneglycol-400 (PEG-400) under microwave irradiation is described. This novel and green protocol p...

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Bibliographic Details
Published inSynthetic communications Vol. 49; no. 16; pp. 2005 - 2016
Main Authors Bayannavar, Praveen K., Kamble, Ravindra R., Shaikh, Saba Kauser J., Kumar, S. Madan, Kumbar, Mahadev N., Nesaragi, Aravind R.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 18.08.2019
Taylor & Francis Ltd
Subjects
Aldehydes
Cascade chemical reactions
Chemical synthesis
Chemistry
Chemistry, Organic
Green synthesis
Irradiation
L-proline
Multicomponent domino reaction
PEG-400
Physical Sciences
Proline
Pyrazole
Reaction time
Science & Technology
Tetrahydroindazolone
ORGANOCATALYST
IDENTIFICATION
DISCOVERY
MICHAEL ADDITION
STRATEGIES
KETONES
POTENT
Multicomponent domino reaction
Tetrahydroindazolone
L-proline
PEG-400
BINDING-AFFINITY
Green synthesis
INHIBITORS
DERIVATIVES
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Summary:A simple and convenient approach for the synthesis of pyrazolyl-tetrahydroindazolones via L-proline catalyzed three component domino reaction of arylhydrazine, dimedone and pyrazole aldehyde in polyethyleneglycol-400 (PEG-400) under microwave irradiation is described. This novel and green protocol proceeds smoothly in good to excellent yields and provides several advantages such as shorter reaction time, metal-free reaction conditions, simple work-up procedures. Also, recycling of the catalyst and solvent was observed without the loss of activity for three (03) runs.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2019.1614628