Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor Agonist

Oxadiazoles

“…1,2,4-Oxadiazole moieties have been used in the design of dipeptidomimetics as peptide building blocks [184a,b]. Compounds 367 contain, at C5 of the 1,2,4-oxadiazole nucleus, a residue of an amino group linked to peptide moieties, and a carboxyl or ester functionality attached at C3 directly or through a methylene chain [293], and 5-HT1D (5-hydroxytryptamine) receptors [294], and as antagonists for 5-HT [295] or histamine H3 receptors [296]. They show activity as antirhinoviral agents [297], growth hormone secretagogues [298], anti-inflammatory agents [234], and antitumor agents [183,188,299].…”

A convenient synthesis of chiral 1,2,4-oxadiazoles from N-protected (α-aminoacyl)benzotriazoles

“…1 Numerous 1,2,4-oxadiazoles have been suggested as potential agonists for cortical muscarinic, 1c,2 benzodiazepine, 3 and 5-HT 1D (5-hydroxytryptamine) receptors, 4 and as antagonists for 5-HT 3 , 5 or histamine H 3 receptors. 6 They show activity as antirhinoviral agents, 1b growth hormone secretagogues, 7 anti-inflammatory agents, 8 and antitumor agents.…”

The reaction of (N‐isocyanimino) triphenylphosphorane with an electron‐poor α‐haloketone in the presence of aromatic carboxylic acids: A novel three‐component reaction for the synthesis of disubstituted 1,3,4‐oxadiazole derivatives

“…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, antiinflammatory, and antihypertensive [5][6][7][8][9].…”