Microwave assisted synthesis of β-keto thioethers and furan derivatives by thiol directed multicomponent reactions

A series of β-keto thioethers tethered with cyclic-1,3-dicarbonyls ( 4 ) has been prepared by a rapid three-component reaction of arylglyoxal, cyclic 1,3-dicarbonlys and thiols in acetic acid medium under microwave heating conditions. Interestingly, under similar reaction conditions, the reaction of...

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Bibliographic Details
Published in:New journal of chemistry 2020-05, Vol.44 (2), p.8442-8453
Main Authors: Jana, Asim, Bhaumick, Prabhas, Choudhury, Lokman H
Format: Article
Language:English
Subjects:
Acetic acid
Crystal structure
Crystallography
Ferric chloride
Furans
Heating
Iron chlorides
Mercaptobenzothiazole
Microwave heating
NMR
Nuclear magnetic resonance
Thermal cycling
Thiols
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Summary:A series of β-keto thioethers tethered with cyclic-1,3-dicarbonyls ( 4 ) has been prepared by a rapid three-component reaction of arylglyoxal, cyclic 1,3-dicarbonlys and thiols in acetic acid medium under microwave heating conditions. Interestingly, under similar reaction conditions, the reaction of phenylglyoxal hydrate, 4-hydroxycoumarin and some thiols such as 4-methoxythiophenol, 2-mercaptobenzothiazole and 2-hydroxythiophenol provides the butterfly like tetra-substituted furan ( 5 ) instead of the corresponding β-keto thioethers 4 . We also have developed an FeCl 3 catalyzed cyclization reaction of β-keto thioethers ( 4 ) for the synthesis of fused furans ( 7 ) under microwave heating conditions. The present work demonstrates how the substituents of thiols and arylglyoxals influence the results of the three-component reaction of arylglyoxal, thiol and cyclic 1,3-dicarbonyls under acidic conditions. A series of β-keto thioethers tethered with cyclic-1,3-dicarbonyls ( 4 ) and a tetra-substituted furan derivative ( 5 ) has been prepared by multicomponent reaction under microwave heating conditions.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj00587h