Passerini multicomponent reaction of indane-1,2,3-trione: an efficient route for the one-pot synthesis of sterically congested 2,2-disubstituted indane-1,3-dione derivatives

Abstract

A reação de Passerini de indano-1,2,3-triona, isocianetos e derivados do ácido benzóico ocorre a temperatura ambiente, conduzindo a derivados estericamente congestionados de indano-1,3-diona 2,2-dissubstituídas em excelentes rendimentos. A reação é limpa, ocorre sob condições brandas e reações laterais não foram observadas.The Passerini reaction of indane-1,2,3-trione, isocyanides and benzoic acid derivatives proceed at room temperature and sterically congested 2,2-disubstituted indane-1,3-dione derivatives are synthesized in excellent yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions are observed.

Triphenylphosphine-Catalyzed Preparation of Sterically Congested, Electron-PoorN-Vinylimidazole Derivatives from Acetylenic Esters and Imidazole-Containing NH-Acids

“…Its ease of workup and reaction conditions make it a useful addition to modern synthetic methodologies. [39][40][41][42][43][44][45][46][47][48][49] Other aspects of this process are under investigation.…”

Ninhydrin in synthesis of heterocyclic compounds

“…There are many published articles on the different reactions of ninhydrin, such as amidoalkylation, 60 Knoevenagel condensation, 61 oxidation, [62][63] reduction, [64][65][66] aldol addition, [67][68][69][70][71][72][73][74] cycloaddition, 75 Friedel-Crafts type reaction, [76][77][78][79][80][81][82][83] Kolbe-Schmitt, 84 Passerini, [85][86][87][88][89][90][91][92] Wittig, [93][94][95][96][97][98][99][100][101][102][103][104][105][106] and Morita-Baylis-Hillman reactions. [107][108][109]…”

Silica Gel Promotes Cascade Synthesis of 2-(Heteroaryl)acetamide Derivatives from Isocyanides, Dialkylamines, and Heteroarylcarbaldehydes

“…[1][2][3] In 1921, Passerini [10] pioneered the use of isocyanides and successfully developed a three-component synthesis of a-acyloxycarboxamides by reaction of carboxylic acid, an aldehyde, and an isonitrile. [11] However, the most important breakthrough came in 1959 when Ugi [12,13] described a four-component synthesis of a -acylamino amides from an aldehyde, an amine, an acid, and an isocyanide.…”