Synthesis of 5-Carboxamide-oxazolines with a Passerini−Zhu/Staudinger−Aza−Wittig Two-Step Protocol

Amidation of Aldehydes and Alcohols through α‐Iminonitriles and a Sequential Oxidative Three‐Component Strecker Reaction/Thio‐Michael Addition/Alumina‐Promoted Hydrolysis Process to Access β‐Mercaptoamides from Aldehydes, Amines, and Thiols

“…In connection with our work on the isocyanide-based multicomponent synthesis of heterocycles, [18] we have reported a one-pot homologation of aldehydes into amides and a-ketoamides. [11] As part of our continued efforts to develop new multicomponent reactions, [19] we were interested in developing oxidative multicomponent reactions, [20][21] and we have recently reported an oxidative three-component reaction of aldehydes 1, amines 2, and trimethylsilyl cyanide (TMSCN) for the synthesis of a-iminonitriles 3, [22] thus making these Abstract: Mild and general aluminapromoted hydrolysis conditions for converting a-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is reported.…”

Passerini Reactions on Biocatalytically Derived Chiral Azetidines

“…Thus we explored other oxidation methods. Also IBX (2-iodoxybenzoic acid), another reagent often used for one-pot oxidative Passerini reactions [16,17,18,19,20], in our hands performed only poorly (entries 4–5) again failing to quantitatively convert 2 .…”

Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications

“…145,146 Recently, the Ugi reaction followed by a postcondensation Staudinger-aza-Wittig reaction was proven to be benecial in the synthesis of several biologically active heterocycles. 147,148 Ding and co-workers reported the rst cyclization of the Ugi product to afford an indolo [1,2-c] and isonitrile was carried out in methanol at room temperature to give Ugi products 307 in fair yield. Ugi products 307 were further reacted with triphenyl phosphine followed by heating in toluene to give the desired indolo[1,2-c]quinazolines 310 (Scheme 66).…”