Reaction of 3-cyanopyridine-2(1H)-thiones with N-butyllithium

The reaction of 3-cyanopyridine-2(1 H)-thiones with BuLi in ether was studied. It was found that the metallation proceeds initially at the sulfur atom. The resulting lithium salts add a second equivalent of n-butyllithium at the CN group. The hydrolysis of the dilithium derivatives leads to 3 pentanoylpyridine-2(IH)-thiones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 231–234, February, 1996.     

Facile Synthesis of 6-Aryl-3-cyanopyridine-2-(1H)-thiones from Aryl Ketones

An improved synthesis of 6-aryl-3-cyanopyridine-2-(1H)-thiones utilizing enaminones as starting materials catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) was described. Moreover, a convenient one-pot conversion of aryl ketones to 6-aryl-3-cyanopyridine-2-(1H)-thiones was also developed in moderate to good yields (up to 80%).     

Synthesis of 1(2H)-Isoquinolones. (Review)

Methods published over the last 10 years for the production of substituted 1(2H)-isoquinolones, including those involving the use of organometallic compounds, are discussed.     

Acetoacetanilides in synthesis of 4-aryl-5-arylcarbamoyl-6-methyl-3-cyanopyridine-2(1H)-thiones

The reaction of acetoacetanilides with arylmethylenecyanothioacetamides leads to 4-aryl-5-arylcarbamoyl-6-methyl-3-cyanopyridine-2(1H)-thiones, based on which we have obtained substituted 2-alkylthiopyridines and thieno[2,3-b]pyridines.     

Regioselective synthesis of 5,6-polymethylene-3-cyanopyridine-2(1H)-thiones and fused heterocycles based on them

Condensation of 2-hydroxymethylenecyclopentan-1-one or -cyclooctan-1-one sodium salts with cyanothioacetamide afforded 5,6-polymethylene-3-cyanopyridine-2(1H)-thiones which were regioselectively alkylated at the sulfur atom by alkyl halides. Derivatives of 3-cyanopyridine-2(1H)-thione and 2-alkylthio-3-cyanopyridine were used for regioselective synthesis of substituted heterocycles: 3-aminothieno[2,3-b]pyridines, pyrido[2,3∶2′,3′]thieno[4,5-d]pyrimidines, and pyrido[2,3∶2′,3′]thieno[4,5-d]oxazines.     

Synthesis and some reactions of 3-cyanopyridine-2-thiones

New methods for the synthesis of 3-cyanopyridine-2-thiones by the reaction of -keto nitroles with sulfur and by condensation of chalcones or benzylideneacetone with cyanothioacetamide are given. The compounds obtained were used in various reactions for the preparation of alkylated products, disulfides, and condensed heterocycles, viz., thieno[2,3-b]pyridines and pyrido[2,3:2,3]thieno[4,5-d]-pyrimidines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 377–382, March, 1981.     

Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*

A method has been developed for the synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones based on the base catalyzed cyclization of N-(3-oxoalkyl)- and N-(3-oxoalkenyl)amides which contain a divalent sulfur atom in an α-position to a carbamoyl group and bound to the heterocycle.     

2-甲基-6-二乙胺基乙氧基-3(2H)-哒嗪酮的合成及其电子性质

分别利用两种方法合成2－甲基－6－二乙胺基乙氧基－3（2H）－哒嗪酮，用^1H NMR,IR,UV和MS进行结构表征，利用ab initio HF和密度泛函理论（DFT）B3LYP方法，对反应物、中间物、产物及其同分异构体进行几何结构的优化和总能量计算，系统分析前线分子轨道特征和能级分布规律，结果表明，2－甲基－6－二乙胺基乙氧基－3（2H）－哒嗪酮比其同分异构体哒嗪氮烷基化合物的能量低，前比后稳定，与实验事实相符合。     

The Synthesis of 3-(2'-Hydroxybutyl) isobenzofuran-1 (3H)-one

l（3H】．Isobenzoturans（Dhthalldes】werereDortedtoexhibitawiderangeofbiologicalactivities．Forexample,3－n－butylphthallde（NB）exhibitsantlasthmatlc’,antlconvuls－ant“actlvltles．PenEandZhouhavestudiedonthemetabolismofNBPInrats‘．Theyfoundthat...     

Synthesis and antioxidative properties of some 3,4-dihydropyrimidin-2(1H)ones (-thiones)

3,4-Dihydropyrimidinones (-thiones) were prepared by ternary condensation of various aromatic aldehydes with ethyl acetoacetate and urea (thiourea) in the presence of trichloroacetic acid in ethanol.     

3-亚甲基异苯并呋喃-1(3H)-酮的合成

以邻甲基苯甲酸甲酯为原料,经过自由基溴代,Wittig反应,酯水解反应,得到邻乙烯基苯甲酸;随后发生环氧化反应,环合反应得到3-羟甲基异苯并呋喃-1(3H)-酮;再发生亲核取代和消除反应合成了3-亚甲基异苯并呋喃-1(3H)-酮。目标产物在空气中长期放置没有发生二聚。化合物结构用1H NMR、13C NMR和IR表征。     

Dibenzotetraazamacroheterocycles: Synthesis and properties. (Review)

Data on the synthesis, complexing ability, practical applications, and biological activity of dibenzotetraazamacroheterocycles of the azacrown ether, amide, and azomethinedibenzotetraazacycloalkane types and also dibenzotetraazamacroheterocycles containing amide and azomethine fragments are classified and analyzed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1763–1796, December, 2005.     

Synthesis of Alkyl 5,6-Dialkyl-2-amino-3-cyanopyridine-4-carboxylates

An unusual route has been found for the hydrolysis of 3-amino-1,1-dialkoxy-6,7-dialkyl-4-aryl-3a,4,5,7a-tetrahydro-1H-pyrrolo[3,4-c]pyridine-3a,7a-dicarbonitriles in acidic medium which leads to the formation of alkyl 5,6-dialkyl-2-amino-3-cyanopyridine-4-carboxylates.