An efficient and regioselective synthesis of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-5-(trihalomethyl)-1H-pyrazoles] from 4-alkoxy-1,1,1-trihaloalk-3-en-2-ones

This work describes the regioselective synthesis of two new series of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-4,5-dihydro-5-hydroxy-5-(trihalomethyl)-1 H -pyrazoles], where the 3-substituents are H, Me, C 6 H 5 , 4-FC 6 H 4 , 4-ClC 6 H 4 , 4-BrC 6 H 4 , 4-NO 2 C 6 H 4 , 4,4′-BiPh, and 2-furyl, in a...

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Bibliographic Details
Published in:Monatshefte für Chemie 2011-03, Vol.142 (3), p.277-285
Main Authors: Bonacorso, Helio G., Cechinel, Cleber A., Navarini, Jussara, Andrighetto, Rosália, Martins, Marcos A. P., Zanatta, Nilo
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Summary:This work describes the regioselective synthesis of two new series of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-4,5-dihydro-5-hydroxy-5-(trihalomethyl)-1 H -pyrazoles], where the 3-substituents are H, Me, C 6 H 5 , 4-FC 6 H 4 , 4-ClC 6 H 4 , 4-BrC 6 H 4 , 4-NO 2 C 6 H 4 , 4,4′-BiPh, and 2-furyl, in a one-pot methodology with ethanol as solvent, from the reaction of 4-alkoxy-4-(alkyl/aryl/heteroaryl)-1,1,1-trihaloalk-3-en-2-ones with oxalyldihydrazide (51–89%). Complementarily, the dehydration reactions of five examples of the described oxalylbispyrazolines are also reported, which furnished the respective 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-5-(trihalomethyl)-1 H -pyrazoles] in 53–78% yields without the two C(O)–N bond cleavages. Graphical abstract .
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-011-0455-0