Nickel boride mediated reductive desulfurization of 2‐thioxo‐4(3H)‐quinazolinones: A new synthesis of quinazolin‐4(3H)‐ones and 2,3‐dihydro‐4(1H)‐quinazolinones

A novel one-pot approach for the synthesis of aryl substituted quinazolin-4(3H)-ones and 2,3-dihydro-4(1H)-quinazolinones has been reported based on the reductive desulfurization of 3-aryl-2-thioxo-4(3H)-quinazolinones with nickel boride in dry methanol at ambient temperature.

[1]  G. Kukreja,et al.  Desulfurization of thioureas, benzimidazoline-2-thiones and 1,3-dihydro-1,3-diaryl-2-thioxopyrimidine-4,6(2H,5H)-diones with nickel boride at ambient temperature , 2002 .

[2]  S. Chauhan,et al.  Facile Reduction of Benzopyrones with Nickel Boride: A New Method for Synthesis of 2H-1-Benzopyran-4-Ols , 2002 .

[3]  G. Kukreja,et al.  RAPID REDUCTION OF NITRILES TO PRIMARY AMINES WITH NICKEL BORIDE AT AMBIENT TEMPERATURE[1] , 2002 .

[4]  S. Chauhan,et al.  RAPID REDUCTION OF CARBONYLS WITH NICKEL BORIDE AT AMBIENT TEMPERATURE[1] , 2001 .

[5]  A. Ray,et al.  Deoxygenation of sulfoxides and selenoxides with nickel boride , 1998 .

[6]  K. Rad‐Moghadam,et al.  One-pot Synthesis of Substituted Quinazolin-4(3H)-ones under Microwave Irradiation , 1998 .

[7]  J. Khurana,et al.  SYNTHETICALLY USEFUL REACTIONS WITH NICKEL BORIDE. A REVIEW , 1997 .

[8]  G. Petrillo,et al.  A novel approach to 1H-indazoles via arylazosulfides , 1994 .

[9]  R. Saladino,et al.  Oxidation of substituted 2-thiouracils and pyrimidine-2-thione with ozone and 3,3-dimethyl-1,2-dioxirane. , 1994 .

[10]  C. Párkányi,et al.  Synthesis of 5-fluoro-2-methyl-3-(2-trifluoromethyl-1,3,4-thiadiazol-5-yl)-4(3H)-quinazolinone and related compounds with potential antiviral and anticancer activity† , 1992 .

[11]  J. F. Wolfe,et al.  Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones. , 1990, Journal of medicinal chemistry.

[12]  C. Panos,et al.  Synthesis of 3,4-dihydro-4-oxoquinazoline derivatives as potential anticonvulsants. , 1983, Journal of medicinal chemistry.

[13]  S. Singh,et al.  SYNTHESIS OF 2-METHYL-3-(3,5-DIALLYL-4-HYDROXYPHENYL)-4-QUINAZOLONES AS POSSIBLE ANTICONVULSANTS , 1978 .

[14]  L. Errede,et al.  Acylanthranils. 4. The effect of steric hindrance on selectivity in the reaction of amines with acetylanthranil , 1977 .

[15]  T. Hisano RECENT STUDIES ON THE MODIFIED NIEMENTOWSKI 4-QUINAZOLONE SYNTHESIS. A REVIEW , 1973 .

[16]  B. Danielsson,et al.  Mass spectrometric investigation of isomeric 1,2,3,4-tetrahydro-4-oxoquinazolines , 1972 .

[17]  T. Kappe,et al.  Synthesen von Heterocyclen, 124. Mitt.: Über Reaktionen des Isatosäureanhydrids mit Thioamiden und Amiden , 1969 .

[18]  T. Kappe,et al.  Synthesen von Heterocyclen, 89. Mitt.: ber Reaktionen des Isatosureanhydrids mit Harnstoff-und Thioharnstoff-Derivaten , 1967 .

[19]  K. Shimada,et al.  [STUDIES ON BENZOHETEROCYCLIC COMPOUNDS. I. SYNTHESIS AND PHARMACOLOGICAL ACTION OF QUINAZOLONE DERIVATIVES]. , 1965, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[20]  J. E. Mccarty,et al.  Synthesis of Some Thioquinazolones of Interest as Potential Ataractic Agents , 1960 .

[21]  H. Stephen,et al.  Syntheses in the quinazolone series—VI: The synthesis of 1:2:3:4-tetrahydro-2-aryl-4-oxoquinazolines , 1957 .

[22]  Gujral Ml,et al.  Comparative evaluation of quinazolones: a new class of hypnotics. , 1955 .

[23]  John F. Meyer,et al.  THE NIEMENTOWSKI REACTION. THE USE OF METHYL ANTHRANILATE OR ISATOIC ANHYDRIDE WITH SUBSTITUTED AMIDES OR AMIDINES IN THE FORMATION OF 3-SUBSTITUTED-4-KETO-3,4-DIHYDROQUINAZOLINES. THE COURSE OF THE REACTION , 1943 .

[24]  E. Wagner,et al.  SOME REACTIONS OF METHYLENE-BIS-AMINES AS AMMONO-ALDEHYDES , 1942 .