Synthesis of Ethyl 4-(1,2,3-Selenodiazol-4-yl)-5-alkylsulfanyl- and -5-Phenylsulphonylmethylfuran-2-carboxylates

Russian Journal of General Chemistry - By means of the reactions of ethyl 4-acetyl-5-bromomethylfuran-2-carboxylate with butanethiol, ethyl sulfanylacetate and sulfanylethanol the corresponding...     

Synthesis of 2-(1,2,3-Thiadiazol-5-yl)-1H-benzimidazoles

We have developed a convenient preparative method for synthesis of previously unknown 2-(1,2,3-thiadiazol-5-yl)-1H-benzimidazoles based on reaction of benzoylhydrazones of 2-acylmethyl-1H-benzimidazoles with thionyl chloride. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1391–1393, September, 2005.     

Synthesis of Glycosides with 4-(4-Hydroxyphenyl)-1,2,3-thia- and -selenadiazole Aglycones

Russian Journal of General Chemistry - Glycosylation of 4-(4-hydroxyphenyl)-1,2,3-thia(selena)diazoles with 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-glucopyranose,...     

Synthesis of 4-(2-Fluoro-4-hydroxyphenyl)-1,2,3-thia- and -Selenadiazoles and Glycosides on Their Base

Russian Journal of General Chemistry - Basing on 2-fluoro-4-methoxyacetophenone 2-fluoro-4-hydroxyphenyl-1,2,3-thiadiazole was synthesized by means of the Hurd-Mori reaction. Under the conditions...     

Selenium heterocycles. XXXVII . Synthesis of 4-(thiazol-4-yl)-1,2,3-selenadiazoles and 4-(selenazol-4-yl)-1,2,3-selenadiazoles

Starting from readily available 2-substituted-4-formylthiazoles and selenazoles, a series of 4-(2-aryl-4-selenazolyl)-1,2,3-selenadiazoles I and 4-(2-substituted-4-thiazolyl)-1,2,3-selenadiazoles II were prepared. Pyrolysis of compound II afforded (2-substituted-4-thiazolyl) acetylenes VII. Addition of potassium hydroxide pellets to an alcoholic solution of II gave 2-substituted-1,4-diselenafulvenes VIII. Decomposition of compound II with base followed by the addition of carbon disulfide gave 5-substituted 2-thioxo-1,3-thiaselenoles XI.     

Synthesis of 2-Substituted 5-(1,2,3-Selenadiazol-4-yl)furan-3-carboxylic Acids Esters

Russian Journal of General Chemistry - A series of semicarbazones have been obtained from 2-substituted 5-acetylfurancarboxylic acid esters. When oxidized with selenium dioxide in acetic acid,...     

Synthesis and Characterization of Novel 2-(1,2,3-Triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles and 2-(4,5-Dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles

Reactions of 1-(5-methyl)-1H-1,2,3-triazol-4-yl)ethan-1-ones and benzaldehydes in ethanol under basic conditions gave the corresponding chalcones. Reactions of the chalcones combined with thiosemicarbazide in dry ethanol containing sodium hydroxide afforded the corresponding pyrazolin-N-thioamides. Reactions of the synthesized pyrazolin-N-thioamides and several ketones (namely, ethyl 2-chloro-3-oxobutanoate, 2-bromoacetylbenzofuran, and hydrazonoyl chloride) gave the corresponding novel 2-(1,2,3-triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles in high yields (77–90%). Additionally, 2-(4,5-dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles were obtained in high yields (84–87%) from reactions with N-pyrazoline-thioamides and 4-bromoacetyl-1,2,3-triazoles under basic conditions. The structures of six of the newly synthesized heterocycles were confirmed by X-ray crystallography.     

Synthesis of ethyl 4-(1,2,3-thiadiazol-4-yl)-5-(bromomethyl)furan-2-carboxylate and its reactions with nucleophiles

By cyclization of carboethoxyhydrazone of ethyl 4-acetyl-5-methylfuran-2-carboxylate under the conditions of Hurd–Mori reaction ethyl 4-(1,2,3-thiadiazol-4-yl)-5-methylfuran-2-carboxylate was synthesized. The ester obtained was brominated with N-bromosuccinimide at the methyl group in the furan ring. This bromide reacts with various N-, S-, O-, and P-nucleophiles to form the corresponding substitution products. Furylthiadiazole fragment remains stable in the course of these transformations.     

Synthesis and Antibacterial Activities of 4-Amino-3-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-5-mercapto-1,2,4-triazoles/2-Amino-5-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles and Their Derivatives

ＩｎｔｒｏｄｕｃｔｉｏｎＳｃｈｉｆｆｂａｓｅｓ ,ａｍｉｄｅｓ ,ｉｍｉｄａｚｏｌｏ[2 ,1 ｂ] 1,3,4 ｔｈｉａｄｉａｚｏｌｅｓ,ａｎｄ 7Ｈ ｓ ｔｒｉａｚｏｌｏ[3,4 ｂ] 1,3,4 ｔｈｉａｄｉ ａｚｉｎｅｓｃｏｎｔａｉｎｉｎｇｈｅｔｅｒｏｃｙｃｌｅｓｈａｖｅｂｅｅｎａｔｔｒａｃｔｉｎｇｍｕｃｈａｔｔｅｎｔｉｏｎａｓｐｏｔｅｎｔｉａｌａｎｔｉｆｕｎｇａｌａｇｅｎｔｓ .1 51,2 ,3 ｔｒｉａ ｚｏｌｅ ,6 7ｍｅｒｃａｐｔｏ 1,2 ,4 ｔｒｉａｚｏｌｅ ,81,3,4 ｔｈｉａｄｉａｚｏｌｅ9 10ａｎｄｔｈｅｉｒｒｅｌａｔｅｄｃｏ…     

4-(2-Aminophenyl)-1,2,3-thia- and -selenadiazoles as a Source of 2-Indolechalcogenolates

Russian Journal of Organic Chemistry -     

Synthesis of 6-(5-sulfanyl-1H-tetrazol-1-yl)-2H-chromen-2-one and 5-methyl-1-(2-oxo-2H-chromen-6-yl)-1H-1,2,3-triazole-4-carboxylic acid

Russian Journal of Organic Chemistry -     

Synthesis and Some Properties of 2-(5-Methyl-2-Phenyl-2H-1,2,3-Diazaphosphol-4-yl)-4H-Benzo[d]-1,3,2-Dioxaphosphorin-4-One

Abstract

2-(5-Methyl-2-phenyl-2Н-1,2,3-diazaphosphol-4-yl)-4H-benzo[d]-1,3,2-dioxaphosphorin-4-one 1 readily reacts with hexafluoroacetone, mesoxalic acid diethyl ester, trifluoropyruvic acid ethyl ester and chloral to give 2-(5-methyl-2-phenyl-2H-1,2,3-dizaphosphole-4-yl)-derivatives of 1,3,2- and 1,4,2-dioxaphosphepines.     

Intramolecular 6-endo-dig-Cyclization of Ethyl 5-Aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate

The reaction of 5-aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid ethyl ester with bases has given ethyl 5-sulfanylidene-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate as a result of intramolecular 6-endo-dig-cyclization of thioketene generated in situ with an internal CH₂NH₂ nucleophile. The obtained ester has been alkylated with iodomethane at the sulfur atom to form ethyl 5-methylsulfanyl-4,7-dihydrofuro[2,3-c] pyridine-2-carboxylate. The Hantzsch reaction with ω-bromoacetophenone has resulted in the formation of 7-ethoxycarbonyl-3-phenylfuro[3,2-d[1,3]thiazolo[3,2-a]pyridin-4-ium bromide.

     

4-(5-喹啉-3-基-四氮唑-2-基)丁胺的合成

三苯基膦钯催化3-溴喹啉完成氰化取代制得3-氰喹啉(1);1与叠氮化钠经[2+3]环加成合成了3-(2H-四氮唑-5-基)喹啉(2);2与N-(4-溴丁基)邻苯二甲酰亚胺反应制得2-[4-(5-喹啉-3-基-四氮唑-2-基)丁基]异吲哚-1,3-二酮(3);3经肼解合成了4-(5-喹啉-3-基-四氮唑-2-基)丁胺(4...     

Synthesis of photoactive 5-aroyl-4-furyl-2-(morpholin-4-yl)thiazoles

5-Aroyl-4-furyl-2-(morpholin-4-yl)thiazoles were synthesized by the reaction of (morpholin-4-ylthiocarbonyl)furan-2-carboxamide with α-bromoketones.     

Synthesis,Crystal Structure and Antimicrobial Activity of Ethyl 2-（1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl）-2-oxoacetate

A novel 1,4,5-trisubstituted 1,2,3-triazole(C18H21N3O3) was synthesized by a one-pot three component reaction of 1-azidocyclohexane, 1-copper(I) phenylethyne and ethoxalyl chloride at room temperature. The molecular structure was determined by single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21/n with a = 12.8167(9), b = 8.0966(6), c = 16.7079(9) , β = 98.716(2)o, Z = 4 and V = 1713.8(2). In the crystal, the molecules are related by inversion and paired into dimers via C–H···O and C–O···C interactions involving(oxo) acetate groups. Furthermore, X-ray analysis results are compared with the optimized structure computed by using B3 LYP method with 6-311 G basis set. The calculated results showed that optimized geometry can well reproduce the crystal structure parameters. The bioassay results indicate that the compound has good antibacterial and antifungal activities.     

N-(4-芳基-噻唑-2-基)--(1H-苯并三唑-1-基)苯乙酮腙类衍生物的合成

以苯并三唑为原料与-溴代芳基乙酮缩合得-(1H-苯并三唑-1-基)芳基乙酮, 再与硫代氨基脲缩合得到新的缩氨基硫脲. 然后分别与5种ω-溴代芳基乙酮环化得到一系列新的含苯并三唑和噻唑环的苯乙酮腙类Schiff碱. 其结构经IR, ¹H NMR, ¹³C NMR和MS及元素分析确证.     

Synthesis and selected transformations of 1-(5-methyl-1-aryl-1H-1,2,3-triazol-4-yl)ethanones and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl]ethanones

By cycloaddition of arylazides to acetylacetone are obtained derivatives of 1,2,3-triazole. In the reaction of 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] ethanones (VIIa-VIIe) with isatin are obtained 2-[1-(R-phenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids (IIIa–IIIe) and 2-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] -4-quinolinecarboxylic acids (IXa, IXb), respectively. We found that 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) readily transform into [5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] acetic acids (IVa–IVc) by the method of Wilgerodt-Kindler. The (5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)acetic acid reacts with 5-phenyl-4-amino-4H-1,2,4-triazol-3-thiol affording 6-[(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) methyl]-3-phenyl[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazole (VI). Original Russian Text ? N.T. Pokhodylo, R.D. Savka, V.S. Matiichuk, N.D. Obushak, 2009, published in Zhurnal Obshchei Khimii, 2009, vol. 79, no. 2, pp. 320–325.