No abstract

Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source.

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic CÀ H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent.

A copper-catalyzed oxidative dehydrogenative reaction of quinoline N-oxides with donor–acceptor cyclopropanes has been demonstrated to construct C2-alkylated quinolines containing a γ-keto diester motif. The use of molecular oxygen as an oxidant, excellent site-selectivity, and good functional group tolerance are the important features in this process. The preliminary mechanistic studies demonstrate that the catalyst plays a dual role as a Lewis acid and a redox catalyst.

2-Deoxy Glycosyl Ortho-[1-(p-MeOPhenyl)Vinyl]Benzoates (PMPVB) donors have been presented as stable, reactive glycosyl donors for the synthesis of 2-deoxy α-glycosides. The donors react under Brønsted acid conditions to provide the 2-deoxy-α-glycosides...