A simple protocol is described for the synthesis of amido and phenyl hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one, and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol-6(2H)-one derivatives via endo-trig (aza-Prins type) cyclization followed by an intermolecular Ritter/Friedel-Crafts reaction of cyclic N-acyliminium ions, which are derived from the boron trifluoride etherate treatment of regioselectively reduced N-homoallyl imides. The reactions are highly diastereoselective with excellent yields.

Herein, we report a mild and efficient hydroxymethylation of quinolines via an iron promoted cross-dehydrogenative coupling reaction under external acid free conditions.

An efficient metal-free one-pot triple functionalization of azaarenes has been developed via a successive regioselective iodination, N-benzylation and amidation by using readily available methylarenes in presence of molecular iodine and TBHP. This method avoids the use of expensive noble metal catalysts and multi-step conversions. Moreover, we have shown the synthetic utility of the iodo functionality with traditional cross-coupling reactions (like Suzuki, Heck and Sonogashira) and the corresponding products were obtained in good yields.

No abstract