Investigation of 2,3'-Biquinolyl. 10. The Regioselectivity of the Reaction of 2,3'-Biquinolyl and 1'-Alkyl-3-(2-quinolyl)quinolinium Halides with Halo Derivatives in the Presence of Metallic Lithium and Magnesium

2,3'-Biquinolyl reacts with halo derivatives in the presence of metallic lithium to give addition products at position 4', treatment of which with water gives 4'-R-1',4'-dihydro-2,3'-biquinolyls and with halo derivatives gives 1'-alkyl-4'-R-1',4'-dihydro-2,3'-biquinolyls. The reaction of 2,3'-biquinolyl with halo derivatives in the presence of metallic magnesium gives a mixture of products of addition at positions 2' and 4'. 1-Alkyl-3-(2-quinolyl)quinolinium halides and halo derivatives with metallic magnesium give 1'-alkyl-2'-R-1',2'-dihydro-2,3'-biquinolyls but form a complex mixture of substances when metallic lithium is used.     

Investigations on 2,3'-Biquinolyls. 15. Regioselectivity of the Addition of Nitromethane Anion to 1'-Alkyl-3'-(2-quinolyl)quinolinium Halides

1'-R-3'-(2-Quinolyl)quinolinium halides react with nitromethane forming products of addition at the position 4', the 1'-R-4'-nitromethyl-1',4'-dihydro-2,3'-biquinolyls. A method has been developed for the synthesis of 1'-phenacyl-1',4'-dihydro-2,3'-biquinolyls based on the alkylation of 1',4'-dihydro-2,3'-biquinolyl with halogen derivatives in DMF.     

Investigations of 2,3′-biquinolyl. 8. Reduction of 1-alkyl-3-(2-quinolyl)-quinolinium halides with sodium borohydride

Reduction of 1-alkyl-3-(2-quinolyl)quinolinium halides with sodium borohydride leads to 1-alkyl-1,2-dihydro-2,3-biquinolyls which, except for the ethoxycarbonyl derivative, undergo rearrangement to 1-alkyl-1,4-dihydro-2,3-biquinolyls. The last can be synthesized by the alkylation of the corresponding 1,4-dihydro-2,3-biquinolyls under conditions of interphase catalysis and in the system KOH-DMSO.For Communication 7, see [1].Stavropol' State University, Stavropol' 355009, Russia; nauka@stavsu.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1084–1087, August, 2000.     

Investigations on 2,3′-Biquinolyl. 16. The Regioselectivity of Reduction of 1-Alkyl-3-(2-quinolyl)quinolinium and 1,1′-Dialkyl-3,3′-di(2-quinolyl)-1,1′,4,4′-biquinolyl Iodides Using Metallic Zinc,Lithium and Potassium

The reaction of 1-alkyl-3-(2-quinolyl)quinolinium iodides with excess zinc in THF gives a diastereomeric mixture of 1,1′-dialkyl-3,3′-di(2-quinolyl)-1,1′,4,4′-tetrahydro-4,4′-biquinolyls. An excess of lithium in THF gives a mixture of 1′,2′-dihydro-2,3′-biquinolyl and 1′-alkyl-1′, 4′-dihydro-2,3′-biquinolyl with the former predominating. The reduction by lithium in THF of 1,1′-dialkyl-3,3′-di(2-quinolyl)-1,1′,4,4′-tetrahydro-4,4′-biquinolyls leads to analogous products. Reduction of 1-alkyl-3-(2-quinolyl)quinolinium iodides by metallic potassium gives 1-alkyl-1′,4′-dihydro-2,3′-biquinolyls. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1208–1212, August, 2005.     

Investigations in the Field of 2,3'-Biquinolyl. 14. Reaction of Dihydro Derivatives of 2,3'-Biquinolyl with Bromine and Iodine

Methods were developed for the synthesis of 6'-bromo- and 6',8'-dibromo-2,3'-biquinolyls and 3',4'-dibromo- and 3',4',6'-tribromo-1'-ethoxycarbonyl-1',2',3',4'-tetrahydro-2,3'-biquinolyls on the basis of the bromination of the dihydro derivatives of 2,3'-biquinolyl. It was shown that the reaction of 1'-alkyl-1',4'-dihydro-2,3'-biquinolyls with bromine and iodine leads to 1'-alkyl-1',2'-dihydro-2,3'-biquinolyl-2'-ones.     

Investigations In the Field of 2,3'-Biquinolyl. 13. Regioselectivity in the Nitration of 2,3'-Biquinolyls and Their 1',4'-Dihydro Derivatives

The nitration of 2,3'-biquinolyls in concentrated sulfuric acid with an equivalent amount of nitric acid at room temperature takes place exclusively at the 2-quinolyl fragment with the formation of the 5- and 8-nitro derivatives or their mixtures. The nitration of the 1',4'-dihydro derivatives under these conditions leads to analogous compounds. Reduction of the nitrobiquinolyls gives the respective amines. Acylation of the latter leads to acylamino-2,3'-biquinolyls.     

2-R-7-Hydroxy-8-methyl-3-(2-quinolyl)chromones

By condensation of 2-methyl resorcinol with 2-quinolyl acetonitrile, we have synthesized α-(2-quinolyl)-2,4-dihydroxy-3-methylacetophenone, which when reacted with carboxylic acid anhydrides followed by hydrolysis yields 2-R-7-hydroxy-8-methyl-3-(2-quinolyl)chromones.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 407–415, March, 2005.     

Facile Iodine(III)-Mediated Approach for the Regioselective Chlorination of 2-Aryl-2,3-dihydro-4(1H)-quinolones

Oxidation of 2-aryl-2,3-dihydro-4(1H)-quinolones (1) with 1.5 equivalents of (dichloroiodo)benzene in dichloromethane at room temperature leads to regioselective chlorination, thereby offering an efficient method for the synthesis of new 2-aryl-6-chloro-2,3-dihydro-4(1H)-quinolones (3).     

Synthesis of 3-(3-Alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl)aminocarbonylchromones

A series of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl)aminocarbonylchromones has been prepared by oxidation of 3-formylchromone with Jones' reagent followed by reaction with 3-alkyl-4-amino-4,5-dihydro-1,2,4-triazole-5(1H)-thione in the presence of POCl³. The structures of the compounds were confirmed by IR, LC-MS, and ¹H NMR spectra and elemental analyses.     

5-(2’-羧乙基)-6-烷基-3,4-二氢吡喃酮的合成

吡喃酮是许多天然产物的结构单元,我们曾由4-异丁酰基庚二酸在过量醋酸酐及乙酰氯存在下回流得到7-氧代-8,8-二甲基-△~9-六氢香豆素.本文由二氰乙基-β-二酮进行酮解水解反应得到4-酰基庚二酸1_(a-c)。 在过量醋酸酐、乙酰氯存在下由1_a、1_c为底物进行反应没有得到双环的香豆素衍生物.其产物和单纯以乙酐为缩合剂时的产物2_a、2_c相同,产率分别为68％、63％。2_c可在硫酸铁催化     

Synthesis of 5-[2-(Phenoxy)ethyl] Derivatives of 6-Methyluracil, 6-Methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one,and 2-Imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one

A synthesis of novel derivatives of 6-methyluracil, 6-methyl-2-thioxo-, and 2-imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one containing a 2-(phenoxy)ethyl substituent at position 5 of the pyrimidine ring has been carried out. It was found that 5-[2-(phenoxy)ethyl] derivatives of 6-methyl-2-thioxo- and 2-imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one are obtained by the condensation of the corresponding ethyl 3-oxo-2-(2-phenoxyethyl)butanoates with thiourea or guanidine. 6-Methyl-5-[2-(phenoxy)ethyl]uracils can be prepared by treating 6-methyl-5-[2-(phenoxy)ethyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-ones with an excess of aqueous monochloroacetic acid solution. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1213–1217, August, 2005.     

Investigations on 2,3′-biquinolyl series. 20. Novel method for the synthesis of 2,3′-biquinolines by cyclization of β-(2-quinolyl)-2-aminostyrenes

A method has been developed for the synthesis of 2,3′-biquinolines based on the reaction of β-(2-quinolyl)-2-aminostyrenes with acid amides under Vilsmeier reaction conditions. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1388–1390, September, 2006.     

3-(2-Quinolyl)- and 3-(5-carbethoxyfuryl-2)coumarins

3-(2-Quinolyl)- and 3-(5-carbethoxyfuryl-2)coumarins were prepared by reaction of substituted salicylaldehydes and hetarylacetonitriles. Alkylation and acylation of 3-hetaryl-7-hydroxycoumarins were studied. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 432–434, September–October, 2005.     

1-(6-硝基-2-苯并噻唑)-3-(5-溴-8-喹啉)-三氮烯与Co(Ⅱ)的高灵敏显色反应及其应用

报道了在CPB 存在下,新试剂1-(6-硝基-2-苯并噻唑)-3-(5-溴-8-喹啉)-三氮烯(NBTBQT)与钴的显色反应.在pH 9.5的硼砂-NaOH缓冲介质中,试剂与钴形成2:1 深蓝色络合物,其最大吸收波长位于655 nm处,表观摩尔吸光系数为1.94×105 L·mol-1·cm-1,钴的质量浓度在0～0.24 mg/L 的范围内符合比尔定律.方法应用于维生素B12注射液和水系沉积物的测定.     

Synthesis of Derivatives of 1-(9-Alkyl-9H-carbazol-3-yl)-4-carboxy-2-pyrrolidinones

Derivatives of 1-(9-alkyl-9H-carbazol-3-yl)-4-carboxy-2-pyrrolidinones (methyl esters, hydrazides) were synthesized. The condensation of the synthesized hydrazides with aromatic aldehydes, acetylacetone, and acetoacetic ester was studied. Structure of the obtained compounds was confirmed by IR and NMR spectroscopy. The specific characteristics of the substituents are discussed.     

Synthesis and Crystal Structure of a New Quinazolinone Compound 2,3-Dihydro-2-（2-hydroxyphenyl）-3-phenyl-quinazolin-4（1H）-one

A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenylquinazolin-4(IH)-one 3 ([C2oH16O2N2]-C2H5OH, Mr = 362.42) and compound 2-(2-hydroxybenzylidene-amino)-N-phenyl-benzamide 2 (C2oH16O2N2, Mr = 316.34) were prepared from a precursor of 2-amino-N-phenyl-benzamide 1 (C13H12ON2, Mr = 212.25). Compound 3 was characterized by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic,space group Pbca with a = 1.2889(11), b = 1.6170(14), c = 1.7729(15) nm, V= 3.695(6) nm^3, Z= 8, F(000) = 1536, Mr = 362.42, Dc = 1.303 g/cm^3, μ(MoKa) = 0.087 mm^-1, R = 0.0447 and wR= 0.0879. The crystal structure analysis indicates that the title compound has a two-dimensional network structure formed by hydrogen bonds and electrostatic interactions.     

新试剂5-(对-苯胺偶氮)-2,3-二氢-1,4-酞嗪二酮的电化学发光研究

应用自制的ECL-1型电致化学发光仪,对新试剂5-(对-苯胺偶氮)-2,3-二氢-1,4-酞嗪二酮(简称ADPD)在Na_2CO_3-NaHCO_3-H_3BO_3缓冲介质中的电化学发光行为作了研究。结果表明,当介质pH值为10.20时,在各种选定的实验条件下,施加+2.0V(vs.SCE)三角波脉冲电压,体系发光强度与ADPD浓度在2×10~(-9)～1×10~(-7)mol/L范围内呈线性关系。反应的检测限为5×10~(-10)mol/L。并且提出了ADPD电化学发光的可能机理。     

Reaction of 2-(2-oxoethylidene)furan-3(2H)-ones with isopropylidenehydrazides of aromatic carboxylic acids: Synthesis of 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones

3-Hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones were obtained by the reaction of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one with benzoic or p-nitrobenzoic isopropylidenehydrazides. Equilibrium C₍₅₎H and C₍₅₎H₂ tautomeric forms were detected in solutions of the 4-chlorophenyl derivatives in DMSO-d₆. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1156–1158, August, 2007.     

Cyanoacetylene and Its Derivatives. 30. Reactions of 2,3-Dimercaptoquinoxaline with 3-Phenyl-2-propynonitrile and 4-Alkyl-4-hydroxy-2-alkynonitriles

The reaction of 2,3-dimercaptoquinoxaline with 3-phenyl-2-propynonitrile (~10 mass % KOH, 20-25°C, 5 h, dioxane) gave the S,S-diadduct (as with unsubstituted acetylene). 2,3-Dimercaptoquinoxaline reacted with 4-alkyl-4-hydroxy-2-alkynonitriles to give 2-cyanomethyl-2-(1-hydroxy-1-alkyl)-1,3-dioxolano[4,5-b]quinoxalines or 3-cyanomethylene-8-imino-2,2,6,6-tetramethyl-1,7-dioxa-4-thiaspiro[4.4]nonane.