Synthesis of Thio and Selenoethers of Cyclic β‐Hydroxy Carbonyls and Amino Uracils: A Metal‐Free Regioselective I2/DMSO Mediated Reaction. Issue 29 (12th October 2017)

• Record Type: Journal Article
• Authors: Jana, Asim; Panday, Anoop Kumar; Mishra, Richa; Parvin, Tasneem; Choudhury, Lokman H.
• Is Part Of: ChemistrySelect. Volume 2:Issue 29(2017)
• Page Start: 9420
• Page End: 9424
• Publication Date: 2017-10-12
• Subjects: Sulfenylation -- Selenylation -- Amino Uracil -- Amino Pyrazole -- Iodine Catalysis -- Metal-free catalyst, C-H activation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201702066
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A simple and practical method has been developed using I2 /DMSO for the construction of C−S and C−Se bonds in pharmaceutically important cyclic β‐hydroxy carbonyls such as 4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one, 4‐hydroxy‐1‐methylquinolin‐2(1H)‐one, quinoline‐2, 4‐diol and heterocyclic enamines such as amino uracil and amino pyrazole derivatives under mild reaction conditions. A series of thio and seleno ethers have been synthesized directly from thiols and selenols in the presence of in situ iodonium ion generated from the I2 /DMSO combination in good to very good yields. This metal‐free dehydrogenative C−S and C−Se coupling reaction goes via C(sp 2 )‐H bond activation and works under conventional as well as microwave heating. Under microwave conditions, reactions complete within 15 minutes with very good yields. Abstract : A simple and practical method has been developed using I2 /DMSO for the construction of C−S and C−Se bonds using directly thiols or selenols with various cyclic β‐hydroxy carbonyls and amino uracils.