Synthesis and reactions of 3-aminothiazolidine-2-thion-4-one derivatives. 1. Conversion of 3-aminothiazolidine-2-thion-4-one derivatives to substituted mercapto-1,3,4-thiadiazoles

The corresponding carboxymethylthiothiadiazoles are formed by the action of formic acid on 3-aminorhodanine and 3-(3-phenylthioureido)rhodanine, and the action of rhodanineaniline on 3-(3-phenylthioureido)rhodanine leads to 2-anilino-5-carboxy-methylthiothiadiazole anilide, whereas similar treatment of 3-ureidorhodanine leads to a semicarbazide derivative.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 51–53, January, 1981.     

Synthesis of 2-sulfanylidene-1,3-thiazolidin-4-one derivatives

Three-component condensation of primary amines with carbon disulfide and dialkyl maleates afforded the corresponding alkyl (3-R-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl)acetates whose structure was confirmed by independent synthesis and IR and ¹H NMR spectroscopy.     

Synthesis of 2-thioxo-1,3-thiazolidin-4-one derivatives

A series of new 2-thioxo-1,3-thiazolidin-4-one derivatives containing arylidene, arylazo, and aminomethylene fragments in position 5 of the rhodanine cycle was synthesized. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1564–1569, August, 2007.     

Synthesis and reactions of 3-aminothiazolidine-2-thion-4-one derivatives. 2. 3-[R-(Alkylthio)methylene]aminothiazolidine-2-thion-4-ones

3-[R-(Alkylthio)methylene]aminothiazolidine-2-thion-4-ones were obtained by the reaction of 3-aminorhodanine with thioimino ester hydriodides.See [1] for Communication 1.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 199–201, February, 1981.     

Synthesis and reactions of 3-aminothiazolidine-2-thion-4-one derivatives. 4. Thiazolo[3,4-b][1,2,4]treiazole derivatives

It is shown that derivatives of a new heterocyclic system, viz., thiazolo[3,4-b][1,2,4]triazole, the structure of which was established by means of their IR and PMR spectra, are formed in the reaction of 5-substituted 3-aminorhodanines with imidoyl chlorides.See [1] for Communication 3.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 331–333, March, 1982.     

Synthesis and reactions of 3-aminothiazolidine-2-thion-4-one derivatives. 3. Reaction of 3-[N-(α-methylthio)ethylidene] aminothiazolidine-2-thion-4-one with amines

It is shown that recyclization leading to the formation of 1,3,4-thiadiazole derivatives occurs in the reaction of 3-[N-(-methylthio)ethylidene]aminothiazolidine-2-thion-4-one with amines. The structures of the compounds obtained were established by spectral methods and were confirmed by alternative synthesis.See [1] for Communication 2.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 339–342, March, 1981.     

Facile synthesis of 3-substituted quinazoline-2,4-dione and 2,3-di-substituted quinazolinone derivatives

3-Substituted quinazoline-2,4(1H,3H)-dione and 2,3-di-substituted quinazolineone derivatives attract considerable interest due to their pharmacological properties. In this paper, we report the synthesis of N-substituted-3-nitrophthalimide derivatives II?CIII, the reactions of phthalimide III with amines, hydrazines, and amino acid derivatives to synthesise a small library of 3-substituted-5-nitroquinazoline-2,4(1H,3H)-diones IV?CXIV and 2,3-di-substituted-6-nitro-quinazolineones XVIII?CXIX.     

Synthesis of novel 1,3-dithiolan-2-one derivatives

Novel 1,3-dithiolan-2-one derivatives were prepared starting from α, β- or β, γ-dichlorinated carboxylic esters and potassium O-ethyl dithiocarbonate. The scope and the mechanism of this reaction were investigated. The biological uses of the compounds obtained here were examined.     

Effect of alkyl chain length, head group and nature of the surfactant on the hydrolysis of 1,3-benzoxazine-2,4-dione and its derivatives

The alkaline hydrolysis of carsalam (2H-1,3-benzoxazine-2,4(3H)-dione), denoted as I, and its N-substituted derivatives i.e., N-methyl-1,3-benzoxazine-2,4-dione (II) and N-benzoyl-1,3-benzoxazine-2,4-dione (III) was studied spectrophotometrically at physiological temperature. The rate of hydrolysis was found to be independent on the substrate concentration. In case of I, the reaction was fractional order with respect to [OH(-)] while for II and III, reaction obeyed the first order kinetics. Effect of cationic surfactants with varying hydrophobic chains (cetyltrimethylammonium bromide, CTAB, tetradecyltrimethylammonium bromide, TTAB and dodecyltrimethylammonium bromide, DTAB) and with different head-group (cetyl pyridinium chloride, CPC) and anionic surfactant (sodium dodecyl sulfate, SDS) was also seen on the rate of alkaline hydrolysis of the carsalam and its derivatives. Cationic surfactants first catalyzed the rate of hydrolysis at lower concentrations followed by the inhibition at higher concentrations. The length of the alkyl chain had remarkable effect on the catalytic efficiency of the surfactants. Similarly N-substitution on substrate also increased the catalysis by micelles. The anionic surfactant SDS inhibited the rate of hydrolysis at all of the concentrations studied. The catalysis by cationic micelles followed by inhibition was treated in terms of the pseudophase ion-exchange model, while for the inhibition by SDS micelles the Menger-Portnoy model was used to fit the data. The effect of salts (NaCl, NaBr and (CH(3))(4)NBr) was also seen on the hydrolysis of II and it was found that all salts inhibited the rate of reaction. The inhibition follows the trend NaCl相似文献   

Synthesis and reactions of 3-aminothiazolidin-2-thion-4-one derivatives. 6. Thiazolo[4,3-b][1,3,4]thiadiazoles

New thiazolo[4,3-b][1,3,4]thiadiazole derivatives were synthesized. The redistribution of the electron density in their molecules during photoexcitation was analyzed by the methods of quantum chemistry.See [1] for Communication 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 484–487, April, 1982.     

Synthesis of adamantane derivatives—38: Synthesis of 1,3-bishoadamantane via ring-expansion of homoadamantan-2-one and homoadamant-4-en-2-one

The ring expansion of homoadamant-4-en-2-one (7) via the corresponding aminomethyl alcohol (9) gave 1,3-bishomoadamant-7-en-4-one (10) as the major product which was converted to 1,3-bishomoadamant-4-ene (14) and 1,3-bishomoadamanta-4,7-diene (16) via the alcohols 13 and 15. Catalytic hydrogenation of 14 and 16 afforded 1,3-bishomoadamantane (2). The ring expansion of homoadamantan-2-one (17) via the aminomethyl alcohol (19) afforded a 9:1 mixture of 1,3-bishomoadamantan-4-one (12) and 5-one (20). The same mixture was also obtained directly from 17 on treatment with diazomethane. The Wolff-Kishner reduction of 12 and 20 gave also 2.     

One-pot synthesis and luminescent spectra of 3-allyl substituted quinazoline-2,4-dione derivatives as allyl capping agents

3-Nitro-N-(phenylsulphonyloxy)phthalimide (IIIa) and N-(phenylsulphonyloxy)phthalimide (IIIb) were synthesised as key intermediates in good yield. Their structures were confirmed by ¹H NMR and FTIR spectral data. The reaction of the key intermediates with allylamine produced 3-allyl-5-nitroquinazoline-2,4-(1H,3H)-dione (IVa) and 3-allylquinazoline-2,4-(1H,3H)-dione (IVb), respectively. Luminescence emission and excitation spectra of IVa and IVb are also presented.     

1,3,5–三嗪–2,4–二酮衍生物的合成及其晶体结构研究

以尿素和4,5-二氮芴-9-酮为原料合成目标化合物,用1 H NMR、元素分析、FT-IR和X-射线单晶衍射进行了表征.晶体结构表明:化合物为单斜晶系,P21/n空间群,晶体学参数:a=0.710 89(9)nm,b=1.507 39(19)nm,c=1.344 95(16)nm,β=99.741(4)°,V=1.420 5(3)nm3,Z=4,Dc=1.591g·cm-3,Mr=339.16,μ=0.472,F(000)=696,R1=0.085 2,wR2=0.274 8[I2σ(I)].化合物通过氢键形成三维网状结构.     

Synthesis and structure of 4-arylspirodihydro-pyranochromen-2-one derivatives

Syntheses are reported for sulfur-and nitrogen-containing derivatives of 4-arylspiro-2-benzopyranones modified at the exocyclic oxygen atom. The structure of these products was demonstrated by correlational NMR spectroscopy. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 518–527, April, 2007.     

4-Azaindane-1,3-dione derivatives. III. Reactivities and prototropic transformations of new 4-azaindane-1,3-diones

New 4-azaindane-1,3-dione derivatives were synthesized from 3-ethoxalyl-5-R-cyclopentane-1,2,4-trione and aliphatic -aminovinylcarbonyl compounds. The halogenation, reduction, and hydrolysis of the synthesized compounds were investigated. The prototropic equilibria of 4-azaindane-1,3-diones were studied.See [1] for communication II.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 256–262, February, 1976.     

Synthesis and reactions of 3-aminothiazolidine-2-thion-4-one derivatives. 5. Polymethine dyes of the thiazolo[3,4-b][1,2,4]triazole series

It is shown that the reaction of thiazolo[3,4-b][1,2,4]triazole-5-thiones with alkylating agents gives 5-methylthiothiazolotriazolium salts, which react with the appropriate intermediates to give polymethine dyes.See [1] for Communication 4.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 480–483, April, 1982.