Reactivity Study on Morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide

• Autoři: FATHALLA Walid; ČAJAN Michal; MAREK Jaromír; PAZDERA Pavel
• Rok publikování: 2002
• Druh: Článek v odborném periodiku
• Časopis / Zdroj: Journal of Heterocyclic Chemistry
• Fakulta / Pracoviště MU: Přírodovědecká fakulta
• Obor: Organická chemie
• Klíčová slova: quinazolines; thioamide reactivity; transamination; oxidative desulfurization; guanidines; thioureas; ab initio (HF/6-31G**) computational analysis
• Popis: Regioselective reactions of morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide (1) with electrophiles and nucleophiles were studied. The compound (1) reacts with alkyl halides in basic medium to afford S-substituted isothiourea derivatives, with amines to give 1,1-disubstituted-3-(2-phenyl-3H-quinazolin-4-ylidene) thioureas and 1-substituted-3-(2-phenyl-quinazolin-4-yl) thioureas via transamination reaction. The reaction of (1) with amines in the presence of H2O2 provided N4-disubstituted-N'4-(2-phenylquinazolin-4-yl)morpholin-4-carboximidamide via oxidative desulfurization. Estimation of reactivity sites on (1) was supported using the ab initio (HF/6-31G**) quantum chemistry calculations. The ir, 1H nmr, 13C nmr, mass spectroscopy and x-ray identified the isolated products.

Související projekty

• Chalkogenorganické sloučeniny - příprava, transformace a strukturní studie
• Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů