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

FATHALLA, Walid, Michal ČAJAN, Jaromír MAREK and Pavel PAZDERA. Reactivity Study on Morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide. Journal of Heterocyclic Chemistry. USA: HeteroCorporation, 2002, vol. 2002, No 39, p. 1145-1152. ISSN 0022-152X.

Basic information

• Original name: Reactivity Study on Morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide
• Authors: FATHALLA, Walid (818 Egypt), Michal ČAJAN (203 Czech Republic), Jaromír MAREK (203 Czech Republic) and Pavel PAZDERA (203 Czech Republic, guarantor).
• Edition: Journal of Heterocyclic Chemistry, USA, HeteroCorporation, 2002, 0022-152X.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• Impact factor: Impact factor: 0.701
• RIV identification code: RIV/00216224:14310/02:00007330
• Organization unit: Faculty of Science
• UT WoS: 000180476400006
• Keywords in English: quinazolines; thioamide reactivity; transamination; oxidative desulfurization; guanidines; thioureas; ab initio (HF/6-31G**) computational analysis
• Tags: guanidines, oxidative desulfurization, quinazolines, thioamide reactivity, thioureas, transamination

Abstract

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.

Links

• GA203/01/1333, research and development project: Name: Chalkogenorganické sloučeniny - příprava, transformace a strukturní studie

Investor: Czech Science Foundation, Chalcogen organic compounds - synthesis, transformation and structure elucidation

• MSM 143100011, plan (intention): Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles