1-Aryl-1-chloro-2,2,2-trifluoroethylisocyanates—convenient reagents for synthesis of 2-aryl-2-trifluoromethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-ones

1-Aryl-1-chloro-2,2,2-trifluoroethylisocyanates react with 3-alkoxyphenols to form N-(1-aryl-2,2,2-trifluoroethylidene)-O-(3-alkoxyphenyl)urethanes, which undergo intramolecular thermal cyclization into derivatives of 2-aryl-2-trifluoromethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-ones.     

Synthesis of some new 3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3-thiazolan-4-ones as antimicrobials

<正>A series of some new 2-imino-5-[(Z)-1-(4-methylphenyl)methylidene]-3-[5-(2-oxo-2H-3-chromenyl)-1,3-oxazol-2-yl]-1,3- thiazolan-4-ones 5a-j has been synthesized and assayed for their antibacterial activity against Gram-positive bacteria viz.Bacillus subtilis(ATCC 6633),Staphylococcus aureus(ATCC 6538p) and Micrococcus luteus(IFC 12708),and Gram-negative bacteria viz. Proteus vulgaris(ATCC 3851).Salmonella typhimurium(ATCC 14028) and Escherichia coli(ATCC 25922).Among the screened compounds,5d,5e,5f,5g,and 5j exhibited potent inhibitory activity compared to standard drug,and emerged as potential molecules for further development.     

Some chemical properties of 2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones

We have studied the reaction of 2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones with amines, alkylating reagents, and hydrogen peroxide. We have shown that the presence of an aryl substituent at the 2 position of [1,3-thiazino[3,2-a]benzimidazol-4-ones has a substantial effect on the direction of the reactions. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 445–452, March, 2006.     

Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles

Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.     

Synthesis of 2-Aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones and 7-Aryl-2,3,6,7-tetrahydro-5H-imidazo[2,1-b]-1,3-thiazin-5-ones

The reaction of 2-mercaptobenzimidazole, 5-ethoxy-2-mercaptobenzimidazole, and 2-mercaptoimidazoline with cinnamoyl chloride, its derivatives, and heteroanalogs was studied. Convenient methods were found for the synthesis of 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones and 7-aryl-2,3,6,7-tetrahydro-5H-imidazo[2,1-b]-1,3-thiazin-5-ones.     

Poly (1,3-[2-methoxy-4-hydroxy-5-acetylphenylene] butylene) (HMAP-BG) as a polymeric ligand

Poly(1,3[2-methoxy-4-hydroxy-5-acetylphenylene]butylene) was prepared by Friedel-Craft polycondensation of 2-hydroxy, 4-methoxyacetophenone and 1,4-butane-diol in presence of poiyphosphoric acid catalyst. The polymer samples were characterized by IR spectra, TGA and their M_n determined by nonaqueous titration. Viscosity measurents in DMSO showed that solutions exhibited normal behaviour. Polymers were complexed with Cu(II), Ni(II), Mn(II), Co(II) and Zn(II) and characterized. Chelation and ion exchange properties were also studied by employing the batch equilibrium method.     

Synthesis of 2-aryl-4-hydroxy-5-thio substituted 1,3-thiazin-6-ones via sulfenylation of 2-aryl-4-hydroxy-[1,3]thiazin-6-ones with sulfenyl chlorides

A series of 2-aryl-4-hydroxy-5-thio substituted 1,3-thiazin-6-ones were synthesized for human immunodeficiency virus-1 protease inhibition. These compounds were synthesized by the treatment of 4-hydroxy-5-thio substituted-1,3-thiazin-6-ones with the corresponding sulfenyl chlorides. The products were obtained in good isolated yields, inspite of the presence of bulkyl substitutents at the ortho position of phenyl sulfenyl chloride portion.     

Synthesis of 5-Amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)- 2,3-dihydro-1H-pyrrol-3-ones*

Reactions of 2-(4-aryl-1,3-thiazol-2-yl)-3-oxo-4-chlorobutyronitriles with primary aromatic amines result in nucleophilic substitution of the chlorine atom by amino group, followed by intramolecular addition of the secondary amino group to the cyano group. The products are 5-amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)- 2,3-dihydro-1H-pyrrol-3-ones which are structurally related to the known antiischemic drugs.     

二[4-羟基-5,6-二氢-6-烷基(芳基)-2H-吡喃-2-酮-3-]烃的合成及生物活性的研究

采用5,6-二氢-6-烷基(芳基)-2H-吡喃-2,4-二酮和醛进行缩合反应,合成了二[4-羟基-5,6-二氢-6-烷基(芳基)-2H-吡喃-2-酮-3-]烃.其结构经¹HNMR和元素分析证实.对反应条件(反应温度、反应时间)进行了探讨.生物活性初步测定表明,该类化合物具有一定的杀菌和抗烟草花叶病毒的活性.     

Synthesis of 5-(perfluoroalkylmethyl)-1,3-dioxolan-4-ones

Acid catalysed condensation of F-alkyl α-hydroxy acids with simple aldehydes or ketones gave F-alkyl 1,3-dioxolan-4-ones. When BF₃,OEt₂ was used as the catalyst, the condensation products were obtained in moderate to good yields and the “cis” isomers are largely favoured, while with HOTs/H₂SO₄ as catalyst, poor yields and lower stereoselectivities were observed.     

Synthesis of 5-[bromo(aryl)methyl]-2,2-dimethyl-1,3-oxazolidin-4-ones

A Darzens condensation of α-chloroacetamide with aromatic aldehydes furnished a series of 3-aryl-2,3-epoxypropionamides, which were further converted to 5-[bromo(aryl)methyl]-2,2-dimethyl-1,3-oxazolidin-2-ones.     

Synthesis of 4-Acyl-5-aryl-3-hydroxy-1-(3-picolyl)-3-pyrroline-2-ones

Russian Journal of General Chemistry - Reaction of methyl esters of acylpyruvic acids with a mixture of aromatic aldehyde and 3-picolylamine gave...     

A New Solution-phase Parallel Synthesis of 2-Alkylamino-3-aryl-5-phenylmethylene-3,5-dihydro-4H-imidazol-4-ones

IntroductionImidazolonesareimportantheterocyclesbearingfungici dal,anti inflammotoryandangiotensinIIantagonisticalactiv ities.1 4 Someof 2 alkylaminoimidazolonesexhibitgoodan tibacterialactivities,5whereasothersshowpotentialantiviralandantitumoractivities.6 Untilnow ,manyofthenewderiva tivesofimidazoloneshavebeensynthesizedtoevaluatetheirbiologicalandpharmaceuticalactivities .Recently ,combinatorialsynthesisoflibrariescontainingsmallorganicmoleculeshasbecomearapidevolvingareaofresearch .7,8…     

A novel and facile synthesis of 2-(cyclohexylamino)-6,7-dihydro-3-aryl-1H-indole-4(5H)-ones via a one-pot multi-component reaction

A simple and efficient synthesis of 2-(cyclohexylamino)-6,7-dihydro-3-aryl-1H-indole-4(5H)-ones was achieved via a one-pot multi-component reaction of cyclohexyl isocyanide, an aldehyde, a 1,3-dicarbonyl compound, and ammonium acetate in the presence of a catalytic amount of KHSO₄ in acetonitrile.     

Synthesis of 5-Alkyl(aryl)-2-alkylsulfanyl(alkoxy)-4-hydroxy-6H-1,3-oxazin-6-ones

Alkyl carbamates and S-alkyl thiocarbamates react with substituted malonyl dichlorides in boiling benzene to give the corresponding 2,5-substituted 4-hydroxy-6H-1,3-oxazin-6-ones. The reaction of S-methyl thiocarbamate with unsubstituted malonyl dichloride in boiling diethyl ether or benzene leads to formation of S-methyl (3-methylsulfanylaminocarbonyl-3-oxopropionyl)thiocarbamate and is not accompanied by cyclization, whereas in boiling toluene 4-hydroxy-2-methylsulfanyl-6H-1,3-oxazin-6-one is obtained.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 3, 2005, pp. 468–472.Original Russian Text Copyright © 2005 by Lalaev, Yakovlev, Zakhs.     

Synthesis of 4-(3-hydroxyalkyl)pyrimidines by ring transformation reactions of 2-alkylidenetetrahydrofurans with amidines

Domino reactions of amidines with 2-alkylidenetetrahydrofurans, prepared by cyclization of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers with various dielectrophiles, provided an efficient access to 4-(3-hydroxyalkyl)pyrimidines.     

Reactions of 5-aryl-4-acyl-1-(4-hydroxyphenyl)-3-hydroxy-3-pyrrolin-2-ones with arylamines

The reaction of 5-(4-chlorophenyl)-4-benzoyl-1-(4-hydroxyphenyl)-3-hydroxy-3-pyrrolin-2-one with aromatic amines affords the corresponding 3-arylamino derivatives, and the reactions of 5-aryl-4-acetyl-1-(4-hydroxyphenyl)-3-hydroxy-3-pyrrolin-2-ones with p-toluidine yield 5-aryl-4-(1-p-tolylamino)ethylene-1-(4-hydroxyphenyl)pyrrolidin-2,3-diones.