856788-15-3Relevant academic research and scientific papers
Synthesis of functionalized fused-ring heterocycles from tautomers of 2-(thiazole, oxazole, benzothiazole, and benzoxazole)-1-phenylethenols and 1,3-diacid chlorides or N-(chlorocarbonyl) isocyanate
De Silva, Hondamuni I.,Chatterjee, Sabornie,Henry, William P.,Pittman, Charles U.
, p. 3453 - 3464,12 (2012/12/13)
2-Methylthiazole, 2,4,5-trimethylthiazole, 2,4,5-trimethyloxazole, 2-methylbenzothiazole, and 2-methylbenzoxazole were each reacted with benzoyl chloride in acetonitrile-triethylamine to generate (Z)-2-(heterocyclic)-1- phenylvinyl benzoates. Base hydrolysis of these vinyl benzoates formed (Z)-2-(heterocyclic)-1-phenylethenols, which exist in both keto and enol tautomeric forms. These tautomers were used as starting materials for fused-ring heterocycle syntheses. Reactions with 2,2-dialkyl-1,3-diacid chlorides in acetonitrile-triethylamine afforded their corresponding 5,6-ring-fused 8-benzoyl-6,6-dialkyl-6H-thiazolo-, 8-benzoyl-2,3,6,6-tetramethyl-6H-thiazolo-, 8-benzoyl-2,3,6,6-tetramethyl-6H-oxazolo-, 4-benzoyl-2,2-dimethyl-1H-benzo[4,5] thiazolo-, and 4-benzoyl-2,2-dimethyl-1H-benzo[4,5]oxazolo[3,2,-a]pyridinedione derivatives. The 5,6,6-tri-ring fused species, 10-benzoyl-7,8-dihydropyrano[2,3- d]thiazolo[3,2-a]pyridin-5(6H)-one, was formed in the reaction of the tautomers of (Z)-1-phenyl-2-(thiazol-2-yl)ethenol with cyclobutane-1,1-dicarbonyl dichloride via a ring expansion after 5,6-ring fusion. Functionalized 5,6-ring-fused 8-benzoyl-6H-thiazolo- and 8-benzoyl-6H-oxazolo[3,2-f]pyrimidine- 5,7-diones, and 4-benzoyl-1H-benzo[4,5]thiazolo- and 4-benzoyl-1H-benzo[4,5] oxazolo[3,2-c]pyrimidine-1,3(2H)-diones were also synthesized by reacting the (Z)-2-(heterocyclic)-1-phenylethenol tautomers with N-chlorocarbonyl isocyanate in THF-triethylamine.
Synthesis of functionalized fused-ring heterocycles from tautomers of 2-(thiazole, oxazole, benzothiazole, and benzoxazole)-1-phenylethenols and 1,3-diacid chlorides or N-(chlorocarbonyl) isocyanate
De Silva, Hondamuni I.,Chatterjee, Sabornie,Henry, William P.,Pittman, Charles U.
, p. 3453 - 3464 (2013/01/15)
2-Methylthiazole, 2,4,5-trimethylthiazole, 2,4,5-trimethyloxazole, 2-methylbenzothiazole, and 2-methylbenzoxazole were each reacted with benzoyl chloride in acetonitrile-triethylamine to generate (Z)-2-(heterocyclic)-1- phenylvinyl benzoates. Base hydrolysis of these vinyl benzoates formed (Z)-2-(heterocyclic)-1-phenylethenols, which exist in both keto and enol tautomeric forms. These tautomers were used as starting materials for fused-ring heterocycle syntheses. Reactions with 2,2-dialkyl-1,3-diacid chlorides in acetonitrile-triethylamine afforded their corresponding 5,6-ring-fused 8-benzoyl-6,6-dialkyl-6H-thiazolo-, 8-benzoyl-2,3,6,6-tetramethyl-6H-thiazolo-, 8-benzoyl-2,3,6,6-tetramethyl-6H-oxazolo-, 4-benzoyl-2,2-dimethyl-1H-benzo[4,5] thiazolo-, and 4-benzoyl-2,2-dimethyl-1H-benzo[4,5]oxazolo[3,2,-a]pyridinedione derivatives. The 5,6,6-tri-ring fused species, 10-benzoyl-7,8-dihydropyrano[2,3- d]thiazolo[3,2-a]pyridin-5(6H)-one, was formed in the reaction of the tautomers of (Z)-1-phenyl-2-(thiazol-2-yl)ethenol with cyclobutane-1,1-dicarbonyl dichloride via a ring expansion after 5,6-ring fusion. Functionalized 5,6-ring-fused 8-benzoyl-6H-thiazolo- and 8-benzoyl-6H-oxazolo[3,2-f]pyrimidine- 5,7-diones, and 4-benzoyl-1H-benzo[4,5]thiazolo- and 4-benzoyl-1H-benzo[4,5] oxazolo[3,2-c]pyrimidine-1,3(2H)-diones were also synthesized by reacting the (Z)-2-(heterocyclic)-1-phenylethenol tautomers with N-chlorocarbonyl isocyanate in THF-triethylamine. Georg Thieme Verlag KG - Stuttgart - New York.
Reactions of keto-enol tautomers of 2-thiazolyl-, 2-oxazolyl-, 2-benzoxazolyl-, or 2-benzothiazolyl-1-phenylethenols with α,β- alkynyl esters: Syntheses of highly functionalized fused-ring heterocycles
De Silva, Hondamuni I.,Henry, William P.,Pittman Jr., Charles U.
supporting information, p. 3337 - 3352 (2013/01/15)
2-Methyl-1,3-thiazole, 2,4-dimethyl-1,3-thiazole, 2,4,5-trimethyl-1,3- thiazole, 2,4,5-trimethyl-1,3-oxazole, 2-methyl-1,3-benzoxazole and 2-methyl-1,3-benzothiazole were each treated with benzoyl chloride in acetonitrile containing triethylamine to give
NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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Page/Page column 136, (2011/04/24)
The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.
