Heterocyclization of Cyanoacetamide Derivatives: Synthesis and Biological Activity of Novel Azoles and Azines

Russian Journal of Organic Chemistry - The intermolecular cyclization of N-benzyl-2-cyanoacetamide with carbon disulfide followed by intramolecular cyclization gave thioxothiazinone 3. This...     

Azines and Azoles: CXXII. New Regioselective Synthesis of 1-Substituted 6-Alkyluracils

Readily available 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones with primary alkyl- and arylamines in mild conditions (boiling in propan-2-ol) to give Schiff bases. In more rigid conditions (boiling in DMF), the reaction is accompanied by COS liberation and provides 1-substituted 6-alkyluracils. This previously unknown reaction possesses a considerable synthetic potential and can be considered as a new, general, and regioselective synthetic approach to 1-substituted 6-alkyluracils.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 1, 2005, pp. 146–158.Original Russian Text Copyright © 2005 by Yuskovets, Moskvin, Mikhailov, Ivin.For communication CXXI, see [1].     

5-芳亚苄基巴比妥酸的固态合成

固相合成;5-芳亚苄基巴比妥酸的固态合成     

Synthetic Studies on Sialoglycoconjugates. 4: Synthesis of 5-Acetamido-3,5-Dideoxy-d-Galacto-2-Octulosonic Acid Derivatives and Analogs

Abstract

5-Acetamido-3.5-dideoxy-D-galacto-2-octulosonic acid derivatives and the α-2-thioanalog (14) were synthesized. Methyl [2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-α-D-galacto-2-octulopyranosid]onate (8), prepared from methyl [2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid]onate (1) via 8,9-O-isopropylidenation, O-acetylation, O-deisopropylidenation, metaperiodate oxidation, and sodium borohydride reduction, was converted, by selective bromination, into the 8-bromo derivatives (9). Compound 12, derived from 8 via O-acetylation and boron trifluoride etherate treatment, was converted to the 2-chloro derivative (13), which underwent displacement with potassium thioacetate, to yield methyl 5-acetamido-4,7,8-tri-O-acetyl-2-S-acetyl-2-thio-α-D-galacto-2-octulopyranosonate (14).     

Synthesis and Antimicrobial Activity of New Thiazole Derivatives and Their Glucoside and Acyclic Nucleoside Analogs

New thiazole derivatives were synthesized. The N‐substituted acyclic nucleoside analogs and the substituted glucosides were also prepared. The synthesized compounds were tested for their antimicrobial activity against Candida albicans, Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The obtained results indicated that most of the tested compounds exhibited low to high moderate activities whereas few compounds were found to exhibit little or no activity against the tested microorganisms.     

Synthesis and Anticancer Activity of New Pyrimidine and Oxadiazole Acyclic Nucleoside Analogs and Thiazolopyrimidine Derivatives

Russian Journal of General Chemistry - A group of new substituted pyrimidine compounds, and their thiazolopyrimidines and 1,3,4-oxadiazolyl acyclic sugar derivatives have been synthesized as...     

Synthesis,Characterization, and in vitro Antibacterial Evaluation of Barbituric Acid Derivatives

Russian Journal of Organic Chemistry - A series of 5,5′-(arylmethylene)bis[1,3-dimethyl-6-(methylamino)pyrimidine-2,4(1H,3H)-diones] have been synthesized by 2: 1 condensation of...     

Synthetic Studies on Sialoglycoconjugates 7: Synthesis of N-Acetylneuraminic Acid Derivatives and Analogs

Abstract

Various types of the O-protected derivatives and the 9-bromo analogs of methyl [2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid]onate were synthesized from methyl [2-(trimethyl-silyl)ethyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid]onate (1) or methyl [2-(trimethylsilyl)ethyl 5-acetamido-8,9-di-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyranosid]onate (3).     

Azines and Their Acyclic Derivatives as Transferers of One-carbon Fragment in Reactions with Pyrazolones

Enehydrazine derivatives have been obtained by the reaction of 6-phenyl-1,2,4-triazine 4-oxide with pyrazolones 2, which on further heating with pyrazolones 2 are converted into the corresponding symmetrical or unsymmetrical derivatives of dipyrazolylmethane. Enehydrazine derivatives of 1,3-dimethyl-5-nitrosouracil and 1,3-dimethylimidazolidine interact with 3-methyl-1-phenyl-5-pyrazolone (2a) with the formation of dipyrazolylmethane derivative. On interacting compound 2a or 3-methyl-1-(p-nitrophenyl)-5-pyrazolone with 3,6-diphenyl-1,2,4-triazine 4-oxide 12 the corresponding 4,4'-bispyrazolones are formed, but the interaction of compound 12 with 3-(p-nitrophenyl)-1-phenyl-5-pyrazolone leads to dipyrazolylmethane derivative. Dipyrazolylmethane derivative is obtained on heating of fervenulin 4-oxide, 2,4-dihydroxy-5-nitropyrimidine, and 1,3,5-triazines: 6-azauracil, 5-azauracil, azacytosine, and 2,4-diamino-s-triazine with pyrazolone 2a.     

Synthetic Studies on Sialoglycoconjugates 7: Synthesis of N-Acetylneuraminic Acid Derivatives and Analogs

ABSTRACT

Various types of the O-protected derivatives and the 9-bromo analogs of methyl [2-(trimethylsilyl)ethyl 5-acetamido-3, 5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid]onate were synthesized from methyl [2-(trimetnyl-silyl)ethyl 5-acetamido-4, 7-di-O-acetyl-3, 5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid]onate (1) or methyl [2-(trimethylsilyl)ethyl 5-acetamido-8, 9-di-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyranosidlonate (3).     

Ketene-S,N-Acetals As Synthetic Intermediates of Heterocycles. New Synthesis of Uracil and Barbituric Acid Derivatives

The importance of enamines for organic synthesis is well documented.¹ Ketene-S,N-acetals2 derived from tertiary thioamides are α-alkylthiosubstituted enamines and expected to work as the synthetic equivalent of an enolate anion³. We have been interested in exploring their synthetic utility as the intermediates of heterocycles.⁴     

FeCl3催化合成巴比妥酸的烷基化衍生物

以苯乙酮和苯甲醛为起始原料,经缩合、还原两步反应合成9个查尔醇（4a~4i）;以FeCl₃为催化剂,室温条件下,在二氯甲烷中实现了1,3-二甲基巴比妥酸与查尔醇4a~4i的烷基化反应,合成了9个巴比妥酸的烷基化衍生物（5a~5i）,其中5b~5i为新化合物,其结构经¹H NMR, ¹³C NMR和HR-MS(ESI)表征。     

Synthesis of Mannich Bases of Meldrum's Acid and Its 5-Substituted Derivatives

Mannich bases of Meldrum's acid and its 5-substituted derivatives were synthesized using aminomethyl acetate or diaminomethane and acetic anhydride as aminomethylating agent.     

Reaction of Barbituric, 2-Thiobarbituric Acids and Their Derivatives with 2-Carboxybenzaldehyde and Opianic Acid: Synthesis and Tautomerism of 5-(3'-Oxo-1',3'-dihydroisobenzofuran-1'-yl)barbituric Acids and Their 2-Thio Analogs

The reaction of barbituric, N-alkylbarbituric acids, and their 2-thio analogs with carboxybenzaldehyde and 2-carboxy-3,4-dimethoxybenzaldehyde leads to the formation of the corresponding 5-(3'-oxo-1',3'-dihydroisobenzofuran-1'-yl)barbituric and 2-thiobarbituric acids, the structures of which were studied by ¹H and ¹³C NMR spectroscopy and mass spectrometry. In DMSO the derivatives of barbituric acid exist in the form of mixtures of the ketone and enol tautomers, while their 2-thio analogs exist in the enol form. In chloroform the tautomeric equilibrium is displaced fully toward the ketone form.     

对甲苯磺酸催化研磨法合成5-芳亚甲基巴比妥酸

在对甲苯磺酸催化下, 将芳香醛与巴比妥酸于室温研磨5～20 min, 则可得到较高收率的5-芳亚甲基巴比妥酸, 为同类化合物的合成提供了一个简便而有效的方法.     

Synthesis of Triterpene Derivatives of D-Glucosamine - Modified Analogs of Glycyrrhizic Acid

Triterpene D-glucosamine amides containing 18α- and 18β-glycyrrhetic acid succinates were synthesized.__________Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 7–9, January–February, 2005.     

以巴比妥酸和蜜胺衍生物为组件构建的一种新型超分子纳米管

纳米有序材料由于其具有特殊性质及广阔的应用前景而倍受人们关注 [1,2 ] .利用分子间非共价键 ,可在原子或分子水平上设计并快速构建具有一定结构和功能的纳米材料 [3,4 ] .目前 ,已合成出包括无机沸石[5] 、石墨 [6] 、类脂组装体 [7] 、生物材料 [8] 及碳 [9] 等多种类型的纳米管 .本文以 5- (4- N-甲基 - N-十四烷基 ) - 2 ,4,6- (1 H,3H) -吡啶三酮 (AB1,14 )和 4-氨基 - 2 ,6-二 (十二烷氨基 ) - 1 ,3,5-均三嗪 (M12 )为原料 ,通过非共价键作用构建出直径～ 7nm,长度为几百纳米的超分子纳米管 .X射线衍射结果表明 ,该纳米管具有 0…     

Synthesis and Antimicrobial Activity of New 1,2,3‐Triazolopyrimidine Derivatives and Their Glycoside and Acyclic Nucleoside Analogs

New [1,2,4‐oxadiazolyl]methyl‐3H‐[1,2,3]triazolo[4,5‐d]pyrimidin derivatives were synthesized starting from N′‐Hydroxy‐1‐naphthimidamide. The N‐substituted acyclic nucleoside analogs as well as the substituted glycosides were also prepared by reaction with the corresponding reagents. The antimicrobial results indicated that most of the tested compounds exhibited moderate to high antimicrobial activity whereas few compounds were found to exhibit little or no activity against the tested microorganisms.     

Thiazolecarboxylic Acid Derivatives. 1. N-Substituted 2-Amino-4-methylthiazole-5-carboxylic Acid Derivatives

Acylation of the ethyl ester and anilide of 2-amino-4-methylthiazole-5-carboxylic acid gave 2-acetyl(arylsulfonyl)amino derivatives. Methylation of acetylaminothiazole and subsequent deacetylation gave 2-methylamino-4-methylthiazole-5-carboxylic acid, which was then converted into esters. The ethyl ester and anilide of thiazole-2-carboxylic acid were used as starting compounds for the synthesis of 2-dimethylaminoformimino- and 2-chlorobenzenesulfonylureido derivatives.     

Chemical Modification of Plant Alkaloids. 2. Reaction of Cotarnine with Barbituric Acid Derivatives and Structure of 5-Dihydrocotarnylbarbituric Acids

The reaction of barbituric acid and its N-substituted derivatives and 2-thio analogs with cotarnine forms 5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-1,3-methylenedioxy-[4,5-g]isoquinolinyl-1)barbituric acids, a new class of zwitter-ions, the structure of which was studied by ¹ H and ¹³ C NMR spectroscopy and mass spectrometry. The prepared compounds exist in solution as stable intermolecular associates and have a complicated H-bonded structure.