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1.
J Org Chem ; 88(22): 15551-15561, 2023 Nov 17.
Article in English | MEDLINE | ID: mdl-37883330

ABSTRACT

A mild, transition-metal-free novel synthetic approach for the construction of C═O and C-N bonds has been demonstrated. Easily accessible gem-dibromoalkenes under similar conditions form oxidative amidation product α-ketoamides and unusual degradative amidation product N-alkyl amides by simply changing the amine substitute. Atmospheric air containing molecular oxygen proved to be an ideal oxidant for an amidation reaction. Under similar conditions, the electron-deficient gem-dibromoalkenes play a dual role with different formamides forming novel oxidative amidation products and by the state of art neighboring group participation of amine to unusual one-carbon degradative amidation products.

2.
J Org Chem ; 87(5): 2410-2420, 2022 03 04.
Article in English | MEDLINE | ID: mdl-35133151

ABSTRACT

A mild, greener approach toward thioamide synthesis has been developed. Its unique features include water-mediated reaction with no input energy, additives, or catalysts as well. The presented protocol is attractive with readily available starting materials and the use of different array amines, along with a scaled-up method. Biologically active molecules such as thionicotinamide and thioisonicotinamide can be synthesized from this procedure.


Subject(s)
Aldehydes , Water , Amines , Catalysis , Temperature
3.
Org Biomol Chem ; 19(11): 2473-2480, 2021 03 21.
Article in English | MEDLINE | ID: mdl-33651057

ABSTRACT

The direct integration of sulphur and amine groups with 1,1-dibromoalkenes for thioamide synthesis has been achieved in an aqueous medium. The presented green protocol emphasizes the suitability of aqueous media for the thioamidation reaction and enables greater selectivity with synthetic utility. A wide range of thioamides in moderate to excellent yields has been achieved using readily available starting materials, with the use of no organic solvents, catalysts, or additives.

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