Synthesis of alkyl 4-aryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylates

Reactions of alkyl acetoacetates, aromatic aldehydes, ammonium acetate, and 1,3-cyclohexanedione afford alkyl 4-aryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylates. The structure of compounds obtained was established with the help of IR, ¹H NMR, and mass spectra and by X-ray diffraction analysis.     

在离子液体中4-芳基-5-氧代-1,4,5,6,7,8-六氢喹啉-3-羧酸酯的合成

以芳醛、氨基巴豆酸酯和5,5-二甲基-1,3-环己二酮或1,3-环己二酮为原料在离子液体[bmimBF₄]中合成了一系列4-芳基-5-氧代-1,4,5,6,7,8-六氢化喹啉-3-羧酸酯, 该方法具有产率高、环境友好等特点. 产物的结构通过红外光谱和核磁共振氢谱进行表征, 并通过X单晶衍射分析进一步证实产物的结构.     

水介质中2,7,7-三甲基-5-氧代-4-芳基-1,4,5,6,7,8-六氢喹啉-3-羧酸乙酯的合成

在水溶剂中有三乙基苄基氯化铵(TEBA)存在下,芳醛、5,5-二甲基-1,3-环己二酮、乙酰乙酸乙酯、醋酸铵四组分混合反应,一步合成了2,7,7-三甲基-5-氧代-4-芳基-1,4,5,6,7,8-六氢喹啉0羧酸酯.该方法具有操作简单、产率高、环境友好的优点.     

Synthesis of 3-cyano-5-ethoxycarbonyl-6-hydroxypyridine-2-thiol derivatives

Ethyl ethoxymethylenemalonate reacts with cyanothioacetamide andN-methylmorpholine to giveN-methylmorpholinium 3-cyano-5-ethoxycarbonyl-6-oxopyridine-2-thiolate. Alkylation of the latter yieldsS-alkyl derivatives. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 196–197, January, 1999.     

Synthesis and Crystal Structure of Ethyl 2,7,7-Trimethyl-4-(4＇-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate in Aqueous Medium

The title compound (C22H27NO3) was obtained by the reaction of 4-methylbenzal- dehyde, dimedone, ethyl acetoacetate and ammonium acetate in water in the presence of triethyl- benzylammonium chloride (TEBA). The crystal is of orthorhombic, space group Pbcn with a = 18.242(2), b = 15.651(1), c = 14.207(2) (A), V = 4056.15(64) (A)3, Mr = 353.45, Z = 8, Dc = 1.158 g/cm3, μ = 0.076, λ(MoKα) = 0.71073 (A) and F(000) = 1520. The final R = 0.0453 and wR = 0.0436 for 1156 observed reflections with I > 2((Ⅰ). X-ray analysis revealed that the pyridine ring is of boat conformation and the six-member ring fused with it adopts half-chair conformation.     

Synthesis and Crystal Structure of Ethyl 2,7,7-Trimethyl-4-(4''''-methylphenyl)- 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3- carboxylate in Aqueous Medium

1 INTRODUCTION The 1,4-dihydropyridines (1,4-DHPs) are biologi- cally interesting compounds and have been developed extensively in pharmacology. 1,4-DHP derivatives are used therapeutically in the treatment of cardio- vascular disorders, especially hypertension and coro- nary heart disease such as angina pectoris, atheros- clerosis, etc. The DHPs have emerged as one of the most important classes of drugs for the treatment of gastrointestinal disease, Raynaud?s disease, pulmonary hyper…     

Synthesis and alkylation ofN-methylmorpholinium 5-cyano-4-(3- and 4-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates

The reactions of 3- or 4-hydroxybenzaldehydes with cyanothioacetamide and Meldrum's acid in the presence ofN-methylmorpholine affordedN-methylmorpholinium 5-cyano-4-(3-or 4-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates, respectively. The resulting compounds were used in the synthesis of substituted 6-alkylthio-1,2,3,4-tetrahydropyridin-2-ones. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2333–2336. December, 1999.     

Synthesis of 4,<Emphasis Type="Italic">N</Emphasis>-diaryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides

Cyclohexane-1,3-dione reacted with substituted benzaldehydes and N-arylacetoacetamides in the presence of ammonium acetate under solvent-free conditions (150–160°C, 10–20 min) to give the corresponding 4,N-diaryl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides. The product structure was determined by IR and ¹H NMR spectroscopy and mass spectrometry.     

Synthesis of 4,n-diaryl-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxamides

The reaction of dimedone, N-aryl-substituted acetoacetic acid amides, aryl aldehydes, and ammonium acetate gives 4,N-diaryl-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-3-quinoline carboxamides.     

无催化剂条件下2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-5,6,7,8-四氢-4H-苯并吡喃的合成

芳亚苄基丙二腈;二甲基环己二酮;无催化剂条件下2-氨基-3-氰基-4-芳基-7;7-二甲基-5-氧代-5;6;7;8-四氢-4H-苯并吡喃的合成     

Synthesis and properties of 5-acetyl-3-cyano-4-isobutyl-6-methyl-3,4-dihydropyridine-2(1H)-thione

Condensation of isovaleric aldehyde with cyanothioacetamide and acetylacetone or its enamine produces 5-acetyl-3-cyano-4-isobutyl-6-methyl-3,4-dihydropyridine-2(1H)-thione, from which 5-acetyl-3-cyano-4-isobutyl-6-methylpyridine-2(1H)-thione and the corresponding substituted 2-alkylthio-1,4-dihydropyridines are prepared. T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011, Ukraine; e-mail: kgb@lgpi.lugansk.ua; N. D. Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow 117913, Russia; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 516–519, April, 1999.     

Crystal Structure and Bovine Serum Albumin Binding Studies of Methyl 4-(2,4-Dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

The title compound, methyl 4-(2,4-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate(C_(20) H_(21)Cl_2NO_3, 1) was synthesized and the crystal structure was —determined by single-crystal X-ray diffraction. It crystallizes in tetragonal system, space group P421 c with a = 16.076(3), b = 16.076(3), c = 14.750(2) ?, V = 3811.8(14) ?3, Z = 8, R = 0.0377 and wR = 0.0845. The interactions between compound 1 and bovine serum albumin(BSA) were investigated using fluorescence spectroscopy. The results revealed that compound 1 can effectively quench the intrinsic fluorescence of BSA by static quenching mechanism. The thermodynamic parameters revealed that the action forces between compound 1 and BSA were mainly van der Waals forces and hydrogen bonds. According to F?rster's non-radioactive energy transfer theory, the binding distance between compound 1 and BSA had been determined. Furthermore, the synchronous fluorescence showed that compound 1 has few effects on the microenvironment and conformation of BSA in the binding process.     

Regioselective Synthesis and Properties of 6-Amino-3-carbamoyl-5-cyano-3,4-dihydrospirocyclohexane-4-pyridine-2-thiol and 5-Cyano-3-thiocarbamoyl-4-spirocyclohexanepiperidine-2,6-dione

Treatment of monothiomalonodiamide with cyclohexylidenemalononitrile or cyclohexylidenecyanoacetic ester in the presence of sodium ethylate gave 6-amino-3-carbamoyl-5-cyano-3,4-dihydrospirocyclohexane-4-pyridine-2-thiol and 5-cyano-3-thiocarbamoyl-4-spirocyclohexanepiperidine-2,6-dione. Their alkylation and hydrolysis have been studied.     

Synthesis and alkylation of 6-methyl-5-phenylcarbamoyl-3-cyano-4-ethylpyridine-2(1H)thione

By condensation of the anilide of acetoacetic acid, propionaldehyde, and cyanothioacetamide, 6-methyl-5-phenylcarbamoyl-3-cyano-4-ethylpyridine-2(IH)thione has been obtained. In an alkaline medium, this compound is alkylated, forming the corresponding substituted 2-pyridyl sulfides. From these pyridines, substituted thienoj2,3-blpyridines have been synthesized through the Thorpe-Ziegler reaction.T. G. Shevchenko Lugansk Pedagogical Institute, Lugansk 348011. N. D. Zelinskii Institute of Organic Chemistry, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1232–1234, September, 1996. Original article submitted May 13, 1996.     

Convenient method for synthesis of functionally substituted hexahydroquinolines. Molecular and crystal structure of 4-isopropyl-7,7-dimethyl-5-oxo-3-cyano-2-cyanomethylthio-1,4,5,6,7,8-hexahydroquinoline

We have obtained 2-alkylthio-7,7-dimethyl-5-oxo-4-ethyl(isopropyl)-3-cyano-1,4,5,6,7,8-hexahydroquinolines by reaction of 5,5-dimethylcyclohexane-1,3-dione, propionic (or isobutyric) aldehyde, cyanothioacetamide, and alkyl halides. We have established the structure of 4-isopropyl-7,7-dimethyl-5-oxo-3-cyano-2-cyanomethylthio-1,4,5,6,7,8-hexahydroquinoline by x-ray diffraction.T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Russian Academy of Sciences, Moscow 117813. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 785–792, June, 1997.     

Synthesis of 3-cyano-5-ethoxycarbonyl-4-isobutyl-6-methyl-3,4-dihydropyridine-2(1H)-thione by three-component condensation

Condensation of isovaleraldehyde with cyanothioacetamide and ethyl acetoacetate (or its enamine) gives 3-cyano-5-ethoxycarbonyl-4-isobutyl-6-methyl-3,4-dihydropyridine-2(1H)-thione. This compound was used in the synthesis of substituted 1,4-dihydropyridin-2-yl sulfides. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 166–168, January, 1999.