One‐Pot Multicomponent Synthesis of β‐Amino Amides

Abstract

Multicomponent reactions are excellent tools for rapid generation of small molecules with broad chemical diversity and molecular complexity. Herein, a novel one-pot multicomponent synthesis of β-amino amides from aldehydes, anilines, carboxylic acids and ynamides has been successfully developed. This process is practical and efficient to unravel synthetic utility and scalability. Moreover, an isotope labeling reaction was conducted to elucidate a plausible reaction mechanism.

Steroid diversification by multicomponent reactions

“…Using cholic acid as carboxylic acid component, Cui and co-workers [37] developed a novel MCR resembling the Ugi-4CR, but relying on the reactivity of ynamides as surrogates of the isocyanide component. Ynamides are alkynes with a carbon–carbon triple bond attached to a nitrogen atom that gives them both nucleophilic and electrophilic properties.…”

Skeletal Reorganization Divergence of N-Sulfonyl Ynamides

“…3c) [63][64] . In continuation of our interests in ynamide chemistry [55][56][57]65 , herein we would like to report an unprecedented skeletal reorganization divergence of N-sulfonyl ynamides for selective entry to thiete sulfones and propargyl sulfonamides ( Fig. 3d).…”

“…Ynamides are type of N-substituted electron rich alkynes which exhibit unique chemical properties and serve as versatile synthons in organic synthesis [33][34][35][36][37][38][39][40][41][42] . For example, ynamides could act as flexible cyclization partners in heterocycle synthesis [43][44][45] , carbene precursors [46][47][48][49] and enamides precursors [50][51] , racemization-free coupling reagents for peptide and macrolide synthesis [52][53][54] , C2 building blocks of multicomponent reactions (MCRs) [55][56][57] . In recent years, the intramolecular cyclizations of ynamides including transition-metal-catalyzed and Brønsted acid-catalyzed nucleophilic cyclizations, anionic cyclizations and radical cyclizations, have been extensively investigated for synthesis of N-heterocycles (Fig.…”

Skeletal reorganization divergence of N-sulfonyl ynamides

“…3c) 63,64 . In continuation of our interests in ynamide chemistry [55][56][57]65 , herein we would like to report a skeletal reorganization divergence of N-sulfonyl ynamides for selective entry to thiete sulfones and propargyl sulfonamides ( Fig. 3d).…”

“…Ynamides are a type of N-substituted electron-rich alkynes that exhibit unique chemical properties and serve as versatile synthons in organic synthesis [33][34][35][36][37][38][39][40][41][42] . For example, ynamides could act as flexible cyclization partners in heterocycle synthesis [43][44][45] , carbene precursors [46][47][48][49] and enamide precursors 50,51 , racemization-free coupling reagents for peptide and macrolide synthesis [52][53][54] and C2 building blocks of multicomponent reactions) [55][56][57] . In recent years, the intramolecular cyclizations of ynamides, including transition-metal-catalysed and Brønsted acid-catalysed nucleophilic cyclizations, anionic cyclizations and radical cyclizations, have been extensively investigated for the synthesis of N-heterocycles ( Fig.…”