One-Pot, Three-Component Synthesis of Dialkyl 1,2-Dihydroquinoline-2,3-Dicarboxylates from Triphenylphosphine, Acetylenic Esters, and Amide Derivatives of 2-Aminobenzaldehyde in Aqueous Acetone

Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives

“…33,34 However, application of 2 in the synthesis of organic compounds has been fairly rare. 25 As part of our ongoing program to develop efficient and robust methods for the preparation of heterocyclic compounds, [35][36][37][38][39][40][41][42][43][44][45] we sought to develop a convenient preparation of 2-aryl-1,3,4-oxadiazoles 5 from 4-substituted benzoic acid derivatives 1 and (N-isocyanimino)-triphenylphosphorane 2 in excellent yields under neutral conditions (Scheme 1). and triphenylphosphine oxide 6 (Scheme 1).…”

“…33,34 In recent years, we have established a one-pot method for the synthesis of organophosphorus compounds. [35][36][37][38][39][40][41][42][43][44] As part of our ongoing program to develop efficient and robust methods for the preparation of heterocyclic compounds (Ali Ramazani reactions), [35][36][37][38][39][40][41][42][43][44][45] we sought to develop a convenient preparation of 2-aryl-1,3,4-oxadiazoles 5 from 4-substituted benzoic acid derivatives 1 and (N-isocyanimino)triphenylphosphorane 2 in excellent yields under neutral conditions (Scheme 1). 1,3,4-Oxadiazoles have attracted interest in medicinal chemistry as surrogates of carboxylic acids, esters, and carboxamides.…”

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

“…[28] This is seen in examples such as the nonsteroidal anti-inflammatory drug (NSAID) lornoxicam, the thiophene analog of piroxicam. [28] As part of our ongoing program to develop efficient and robust methods for the preparation of organic compounds, [29][30][31][32][33][34][35][36][37][38][39] we sought to develop a convenient preparation of sterically congested 2-(heteroaryl)acetamide derivatives 7 from an isocyanide, a secondary amine, and heteroarylcarbaldehydes in the presence of silica gel at room temperature in excellent yields under neutral conditions (Scheme 1).…”

Four-Component Preparation of Disubstituted 1,3,4-Oxadiazoles from (N-isocyanimino)triphenylphosphorane, Phenylacetylenecarboxylic Acid, Biacetyl and Primary Amines

“…16,17 In recent years, we have confirmed a one-pot method for the preparation of organophosphorus compounds. [18][19][20][21][22][23][24] As part of our ongoing program to develop efficient and robust methods for the preparation of heterocyclic compounds, [25][26][27][28][29][30][31][32][33][34][35][36][37][38] we wish to report the preparation of a new class disubstituted 1,3,4-oxadiazole derivatives 5a-j by a novel four-component condensation reaction of biacetyl (1), primary amine 2, (Nisocyanimino)triphenylphosphorane (4) and phenylacetylenecarboxylic acid (3) in excellent yields under neutral conditions (Scheme 1).…”