Efficient one‐pot synthesis of disubstituted 1,3,4‐oxadiazole derivatives from the reaction of (N‐isocyanimino)triphenylphosphorane, acetaldehyde, a secondary amine, and an electron‐poor (E)‐cinnamic acid

The reaction of (N‐isocyanimino) triphenylphosphorane with (E)‐3‐aryl‐2‐ propenoic acid derivatives: One‐pot synthesis of 2‐[(E)‐2‐aryl‐1‐ethenyl]‐1,3,4‐oxadiazoles via intramolecular aza‐Wittig reaction

“…However, application of 2 in the synthesis of organic compounds has not been reported. As a part of our ongoing program to develop efficient and robust methods for the preparation of heterocyclic compounds [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28], we sought to develop a convenient preparation of 2-[(E)-2-aryl-1-ethenyl]-1,3,4-oxadiazole 3 from (E)-3-aryl-2-propenoic acid derivatives 1 and (N-isocyanimino)triphenylphosphorane 2 in fairly good yields in neutral conditions. The reaction is completely stereoselective (Scheme 1).…”

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

“…Its ease of workup and good yields makes it a useful addition to modern synthetic methodologies. [44][45][46][47][48][49][50][51][52][53][54][55] EXPERIMENTAL Starting materials and solvents were obtained from Merck (Germany) and Fluka (Switzerland) and were used without further purification. The methods used to follow the reactions were TLC and NMR.…”

The Reaction of N-Isocyaniminotriphenylphosphorane with 2-Oxopropylbenzoate (or 4-Bromobenzoate) and a Primary Amine in the Presence of (E)-Cinnamic Acid Derivatives: A One-Pot Efficient Four-Component Reaction for the Synthesis of 2-(Arylamino)-2-(5-aryl

“…1,3,4‐Oxadiazoles have attracted interest in medicinal chemistry as surrogates of carboxylic acids, esters, and carboxamides. They are an important class of heterocyclic compounds that have a wide range of pharmaceutical and biological activities including antimicrobial, antifungal, anti‐inflammatory, and antihypertensive .…”