Synthesis of 1,2,3,4‐tetrahydroquinazoline derivatives as potential alpha‐adrenergic blocking agents

Abstract

The synthesis of N,N′‐bis[6‐(1,2,3,4‐tetrahydro‐3‐quinazolidyl)hexyl]cystamine (I) and 3‐(6‐aminohexyl)‐1,2,3,4‐tetrahydroquinazoline (II) are described. Compound I is obtained by condensation of o‐nitrobenzoyl chloride with 3‐(6‐aminohexyl)‐1,3‐thiazolidine (III) followed by dimerization, reduction and formation of tetrahydroquinazoline ring. A similar method was used for preparation of compound II. These compounds and some synthesis intermediates are potential alpha‐adrenergic blockers.

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

“…Pyrimidine and its saturated or partially saturated derivatives have a wide range of biological activity, which makes them desirable synthetic targets [204][205][206][207]. The condensation of propylenediamine with 3 equiv.…”

New Vanadium Keggin Heteropolyacids Encapsulated in a Silica Framework: Recyclable Catalysts for the Synthesis of Highly Substituted Hexahydropyrimidines Under Suitable Conditions

“…Also, the hexahydropyrimidine skeleton occurs in alkaloids such as tetraponerines, verbametrine and verbamethine, which are synthetic intermediates for spermidine-nitroimidazole drugs, and is used for the treatment of A549 lung carcinoma [26]. Benzo-fused hexahydropyrimidines possess antiplatelet activity [27] and are potential R-adrenergic blockers [28].…”

Superparamagnetic Iron Oxide as an Efficient Catalyst for the One‐Pot, Solvent‐Free Synthesis of 5,5‐Disubstituted Hexahydropyrimidines and Their Spiro Analogues

“…N-Substituted hexahydropyrimidines are synthetic intermediates for recently discovered spermidine-nitroimidazole drugs for the treatment of A549 lung carcinoma [4] and structural units in new trypanothion ereductase inhibiting ligands for the regulation of oxidative stress in parasite cells [5]. Benzo-fused hexahydropyrimidines or 1,2,3,4-tetrahydroquinazolines are potential R-adrenergic blockers [6] and possess antiplatelet activity [7]. Hexahydropyrimidines are prepared classically by condensations of substituted propane-1,3-diamines with aldehydes and ketones [8,9].…”