Reaction of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones with acetylacetone and methyl acylpyruvates

Aroyl ketenes formed in the thermolysis of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones undergo a [4+2]-cycloaddition reaction with acetylacetone and methyl acylpyruvates to give 2-methyl- and 2-methoxycarbonyl-3-acyl-6-arylpyran-4-ones, respectively.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 161–163, February, 1989.     

Formation of pyrimidin-4-one derivatives in the reaction of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones with ketene aminals

N. D. Zelenskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 5, pp. 1225–1226, May, 1992.     

6-Aryl-2,2-dimethyl-1,3-dioxin-4-ones: Synthesis and Chemical Characteristics. (Review)

Methods for the production of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones and their thermolysis in the presence of nucleophiles and dienophiles are discussed     

Hetero-diels-alder reaction of N-cyanoaniline and pyridinium cyano-(ethoxycarbonyl)methylide with aroylketenes generated in situ in thermolysis of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones

We have used thermolysis of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones in the presence of N-cyanoaniline, pyridinium cyano(ethoxycarbonyl)methylide, and 4-hydroxybenzonitrile to obtain the corresponding 6-aryl-2-phenylamino-1,3-oxazin-4-ones, pyridinium ethoxycarbonyl(4-oxo-6-aryl-4H-1,3-oxazin-2-yl)methylides, and p-cyanophenyl esters of 3-aryl-3-oxopropanoic acids. We present the results of a preliminary investigation of the biological activity of these compounds. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 764–768, May, 2006.     

Facile syntheses of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the corresponding 6-substituted 4-hydroxy-2-pyrones

A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-l. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.     

A simple synthesis of functionalized pyridines from 6-aryl-1,3-dioxin-4-ones and N-benzoylaminal of monoacetylketene

Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 234–235, January, 1993.     

A simple synthesis of functionalized pyridines from 6-aryl-1,3-dioxin-4-ones and N-benzoylaminal of monoacetylketene

Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 234–235, January, 1993.     

Asymmetric reduction of 2,2-dimethyl-6-(2-oxoalkyl/oxoaryl)-1,3-dioxin-4-ones and application to the synthesis of (+)-yashabushitriol

The asymmetric transfer hydrogenation of a series of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and 2,2-dimethyl-6-(2-oxoaryl)-1,3-dioxin-4-ones was achieved in high enantiomeric excess using a Ru(II) catalyst. The aryl substrates were most compatible with the methodology and this process facilitated a total synthesis of enantiomerically pure (+)-yashabushitriol.     

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.     

An efficient and rapid synthesis of β-carboxamide derivatives using 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones by microwave irradiation

A general, efficient and rapid method for the synthesis of various β-carboxamide derivatives using microwave irradiation is described. Excellent isolated yields were obtained in very short reaction times when conventional heating was replaced by microwave irradiation.     

Azoles and azines: CXXVIII. Reaction of 2-aryl-4-hydroxy-6H-1,3-thiazin-6-ones with 6-bromo-4-oxo-4H-chromene-3-carbaldehyde

Russian Journal of General Chemistry -     

5-Amino-4-aryl-2,2-dimethyl-1,3-dioxans: application as chiral NMR shift reagents and derivatizing agents for acidic compounds

The use of (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxan (ADPD) and (4R,5R)-5-amino-(4′-biphenyl)-2,2-dimethyl-1,3-dioxan (ABDD) as chiral solvating agents (CSA) for the ee determination of compounds bearing an acidic proton by means of ¹H NMR spectroscopy is demonstrated. In addition, based on the well known rigid conformation of these amines, ADPD and ABDD are suitable as chiral derivatizing agents (CDAs) in order to determine absolute configurations.     

1,3-二甲基-4-芳氧乙酰基-5-吡唑啉酮类化合物的合成

以双乙烯酮和甲基肼为原料合成1,3-二甲基-5-吡唑啉酮, 再在氢氧化钙催化下,以异丙醇为溶剂, 与芳氧基乙酰氯缩合制得一纱列标题化合物. 并用红外, 紫外, 质谱研究了它们的结构 . 测定了它们对于家稗的生物活性, 探讨了除草活性与结构的关系.     

Reaction of dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with aliphatic amines

Benzylamine, phenethylamine, and homoveratrylamine reacted with dialkyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates at the endocyclic carbonyl group with conservation of the enolic hydroxy group to give dialkyl 4-alkylamino-2-aryl-6-hydroxy-6-methylcyclohex-3-ene-1,3-dicarboxylates. The reaction of dimethyl 4-hydroxy-4-methyl-6-oxo-2-phenylcyclohexane-1,3-dicarboxylate with tryptamine was accompanied by dehydration with formation of dimethyl 4-[2-(1H-indol-3-yl)ethylamino]-6-methyl-2-phenylcyclohexa-3,5-diene-1,3-dicarboxylate, presumably due to basic properties of the indole nitrogen atom.     

Reaction of zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones with 2-arylmethylidenemalononitriles

Zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones react with 2-arylmethylidenemalononitriles to give 2-alkyl-3-aryl-2-aroylcyclopropane-1,1-dicarbonitriles.     

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.     

Reaction of 4-Methylene-1,3-dioxolan-2-ones with Hydrazines

The structure of the products of the reaction of 4-methylene-1,3-dioxolan-2-ones with hydrazines is a function of the structure of the starting hydrazine. 1,3,4-Oxadiazin-2-one derivatives are obtained from hydrazine hydrate. 3-Arylaminooxazolidin-2-ones are obtained from monoarylhydrazines, while mixtures of these derivatives are obtained from aliphatic monoalkylhydrazines.