Iodine–TBHP mediated efficient synthesis of α-ketoamides from vinyl azides and amines under mild conditions

Abstract

A convenient and practical synthetic approach for α-ketoamides has been developed under mild condition. The facile synthesis of α-ketoamides has been accomplished using aryl vinyl azides and secondary amine at...

Vinyl azides in organic synthesis: an overview

“…This reaction can be seen in Scheme 86. 5 α-Ketoamides and their derivatives are present in a variety of natural products, biologically active molecules such as antitumor, anti-IBD, 98 antiviral, 99 anti-HIV, 100 and antibacterial drugs, and functional materials. The α-ketoamide moieties are also present in diverse pharmacologically interesting compounds, as shown in Fig.…”

“…7. 5 In the possible mechanism, in the presence of I 2 , N-unsubstituted imine 306 would rst be generated from a-aryl vinyl azides, with the release of N 2 . Then, aq.…”

“…α-Substituted vinyl azides have been utilized as radical acceptors to produce a variety of molecules, including α-trifluoro methylated ketones, α-trifluoromethyl azines, keto sulfones, α-azido styrene, cyclic β-amino ketones, N -unprotected enamines, enaminones, β-keto phosphine oxides, unsymmetrical ketones, and 2-aryacetophenones. 5…”

“…a-Substituted vinyl azides have been utilized as radical acceptors to produce a variety of molecules, including a-triuoro methylated ketones, a-triuoromethyl azines, keto sulfones, a-azido styrene, cyclic bamino ketones, N-unprotected enamines, enaminones, b-keto phosphine oxides, unsymmetrical ketones, and 2aryacetophenones. 5 It has also been observed that vinyl azides can serve as multipurpose precursors for the synthesis of various units through diverse cleavages. Units generated from different cleavages are shown in Fig.…”

Construction of C(CO)–C(CO) Bond via NHC-Catalyzed Radical Cross-Coupling Reaction

“…Furthermore, the reaction in the presence of NHC-1 provided sterically congested α-keto amide 3r in 54% yield. These results demonstrate advantage over a few protocols of synthesizing α-keto amides through the electron pair mechanism, which are problematic for challenging hindered substrates . In addition to providing the normal product, α-keto amide 3s , in 40% NMR yield, the reaction with 2-iodobenzoyl fluoride afforded the deiodinated byproduct 3a in 16% NMR yield.…”