N-Oxide-Induced Ugi Reaction: A Rapid Access to Quinoline-C2-amino Amides via Deoxygenative C(sp2)-H Functionalization.

A logic-based replacement of the carboxylic acid component of the Ugi reaction by quinoline N-oxides has been developed. In this approach, the carboxylic isostere, quinoline N-oxide, plays a vital role by shifting the equilibria toward the product side with irreversible addition onto the C2-position of the N-oxide. Thus, aldehydes react with amines, isocyanides, and quinoline N-oxides to furnish quinoline four-component Ugi adducts. The unique reactivity of N-oxides with Ugi components opens an efficient synthetic route for the preparation of biologically active compounds.

Rongalite-induced transition-metal and hydride-free reductive aldol reaction: a rapid access to 3,3'-disubstituted oxindoles and its mechanistic studies.

A transition-metal and hydride-free reductive aldol reaction has been developed for the synthesis of biologically active 3,3'-disubstituted oxindoles from isatin derivatives using rongalite. In this protocol, rongalite plays a dual role as a hydride-free reducing agent and a C1 unit donor. This transition metal-free method enables the synthesis of a wide range of 3-hydroxy-3-hydroxymethyloxindoles and 3-amino-3-hydroxymethyloxindoles with 79-96% yields. One-pot reductive hydroxymethylation, inexpensive rongalite (ca. $0.03/1 g), mild reaction conditions and short reaction time are some of the key features of this synthetic method. This protocol is also applicable to gram scale synthesis.