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 alkylation of 3-cyano-4-isobutyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-2-thiol

By reaction of isovaleric aldehyde with cyanothioacetamide and cyclohexane-1,3-dione, 3-cyano-4-isobutyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-1-thiol has been obtained, and subsequently used in synthesis of the corresponding substituted 2-alkylthiohexahydroquinolines.Lugansk T. G. Shevchenko State Pedagogical Institute, Lugansk 348011, Ukraine. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 230–231, February, 1999.     

Synthesis and structure of 3-allenyl-4-aryl-7,7-dimethyl-5-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinoline-3-carbonitriles

3-Allenyl-4-aryl-7,7-dimethyl-5-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinoline-3-carbonitriles were synthesized via [3,3]-sigmatropic rearrangement of 4-aryl-7,7-dimethyl-5-oxo-2-(prop-2-yn-1-ylsulfanyl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitriles. The structure of 3-allenyl-7,7-dimethyl-4-(2-nitrophenyl)-5-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinolin-3-carbonitrile was determined by X-ray analysis.     

微波辐射下4-芳基-7,7-二甲基-5-氧代-3,4,5,6,7,8-六氢 香豆素的合成及其晶 体结构

芳醛(1),5,5-二甲基-1,3-环已二酮(2),麦氏酸(3)经微波辐射3～5min,不需任何催化剂,得到4-芳基-7,7-二甲基-5-氧代-3,4,5,6,7,8-六氢香豆素(4)。产物的结构经红外、核磁、元素分析及X-射线衍射法确证。对反应过程提出了可能的机理。     

A convenient method for the synthesis of substituted 2-alkylthio-3-cyano-4,6-dimethyl-5-phenylcarbamoyl-1,4-dihydropyridines

Substituted 2-alkylthio-3-cyano-4,6-dimethyl-5-phenylcarbamoyl-1,4-dihydropyridines were obtained by successive reaction of acetaldehyde with cyanothioacetamide and acetoacetanilide, -chloracetamide or phenacyl bromide in the presence of piperidine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 345–347, March, 2000.     

水中"一锅法"合成2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃

报道了以十二烷基苯磺酸(DBSA)为催化剂,芳醛、丙二腈和5,5-二甲基-1,3-环己二酮为原料于水中一步生成2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃.该方法具有产率高、操作简便、对环境友好、催化剂可重复使用等优点.     

水中2-氨基-3-氰基-4-芳基-7，7-二甲基-5-氧代4H-5，6，7，8-四氢苯并[b]吡喃的洁净合成

在水溶剂中在三乙基苄基氯化铵（TEBA）存在下，取代肉桂腈与5，5-二甲基- 1，3-环已酮反应为2-氨基-3-氰基-4-芳基-7，7-二甲基-5-氧代-4H，5，6，7，8- 四氢苯并[b]吡喃提供了一种快速、方便、高效和洁净的合成方法。     

Synthesis of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids

2-Substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids were synthesized by reaction of acyl- and aroylpyruvic acids with 3-amino-5,5-dimethylcyclohex-2-en-1-one. A plausible mechanism of their formation was proposed on the basis of ab initio quantum-chemical calculations.     

Microbiological synthesis of 4-hydroxy-5-isopropyl-5-methoxy-2-oxo-2,5-dihydrofuran

M. V. Lomonosov Moscow State University, Moscow 119899, and Chemistry Section, Leipzig University, 7062 Leipzig, Germany. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 711–712, May, 1994.     

2-氨基-3-氰基-7,7-二甲基-4-苯基-5-氧代-5,6,7,8-四氢-4H-苯并吡喃的合成和晶体结构

标题化合物C18H18N2O2是由亚苄基丙二睛和5,5-二甲基-1,3-环己酮在乙二醇中反应2小时得到,结构通过单晶X-射线衍射法确定,其晶体属单斜晶系,空间群P21/c,Mr=294.34,a = 11.3070(1), b= 9.4750(1),c = 14.919(2) ,β= 99.34(1)埃琕 = 1577.1(3) 3,Z = 4,Dc=1.240Mgm-3,μ=0.082mm-1,F(000)=624, 最终的偏离因子为R=0.0381,wR=0.0961,在分子结构中存在3个环:苯环(A)、吡喃环(B)及与吡喃环稠合的六员环(C)。A与B、A与C及B与C之间的两面角分别为 92.5°、85.7°和8.2°。     

微波辐射下2,7,7-三甲基-3-乙氧羰基-4-(3-硝基苯基) -5-氧代-1,4,5,6,7,8-六氢喹啉的合成和晶体结构

标题化合物C21H24N2O5是由间硝基苯甲醛、达咪酮、乙酰乙酸乙酯、醋酸铵在微波辐射下干反应而得。结构通过单晶X-射线衍射法确定,其晶体属斜方晶系,空间群 Pbcn, a =17.953(3), b =15.206(4), c =14.299(3), V =3904.(2)3, Mr =384.42, Z =8, Dc =1.308g/cm3 , m(MoKa) =0.094mm-1, F(000)=1632。晶体结构用直接法解出,经全矩阵最小二乘法对原子参数进行修正,最终的偏离因子为R=0.0493, wR=0.1078。X-射线分析结果表明,吡啶环为船式构象,与之稠合的六元环为信封式构象。     

KF-蒙脱土催化下2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃的合成

以KF-蒙脱土为催化剂, 取代肉桂腈与5,5-二甲基-1,3-环己二酮在95%乙醇中回流反应得2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并[b]吡喃, 此方法快速、方便、高效, 同时考察了溶剂、催化剂对反应的影响.     

超声辐射下一步法合成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[b]吡喃

芳醛、丙二腈和5，5-二甲基-1，3-环己二酮在乙二醇中不加任何催化剂经超 声辐射5-7min得2-氨基-3-氰基-4-芳基-7，7-二甲基-5-氧代-4H-5，6，7，8-四氢 苯并[b]吡喃，产率88％—96％．     

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.     

Crystal and molecular structure of 7,7-dimethyl-2,3-di(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline

An x-ray crystallographic investigation of 7,7-dimethyl-2,3-di(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline, obtained by the hydrolysis of its oxime, was undertaken. The oxime, together with the isomeric oxime of 7,7-dimethyl-2,4-di(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline, is formed in the reaction of 5,5-dimethyl-2-[1,3-di(4-methoxyphenyl)-3-oxopropyl]cyclohexane-1,3-dione with hydroxylamine hydrochloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1085–1088, August, 1987.     

Regioselective synthesis and properties of 3-cyano-6-methyl-4-trifluoromethylpyridine-2(1H)-thione. Molecular and crystal structure of 3-cyano-2-ethylthio-6-methyl-4-trifluoromethylpyridine

The reaction of trifluoroacetylacetone with cyanothioacetamide proceeded regioselectively to form 3-cyano-6-methyl-4-trifluoromethylpyridine-2(1H)-thione from which the corresponding 2-alkylthiopyridines and 3-aminothieno[2,3-b]pyridines were obtained. The crystal and molecular structure of 3-cyano-2-ethylthio-6-methyl-4-trifluoromethylpyridine was established by X-ray diffraction analysis.     

Synthesis and reactions of 2-(4-pyridyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinazoline

7,7-Dimethyl- and 7-phenyl-2-(4-pyridyl)-5-oxo-5,6,7,8-tetrahydroquinazolines were synthesized in the reactions of 2-formyl-5,5-dimethyl- and 5-phenyl-1,3-cyclohexanediones, respectively, with 4-amidinopyridine. The oxime, thiosemicarbazone, 4-quinazolyl-, nicotinoyl-, isonicotinoyl-, and 2-hydroxybenzoylhydrazones of 2-(4-pyridyl)-5-oxo-7,7-dimethyl-5,6,7,8-tetrahydroquinazoline were obtained. The reduction of this ketone by sodium borohydride leads to the 5-hydroxy derivative.