Synthesis of 8-arylsulfoxyl/sulfonyl adenines

We report a method for the synthesis of 9-N-alkyl-8-arylsulfoxyl adenines and 9-N-alkyl-8-arylsulfonyl adenines. The approach starts with a tandem one-pot reaction that by using Mitsunobu conditions converts 8-arylsulfanyl adenines to the corresponding iminophosphorane protected 9-N-alkyl-8-arylsulfanyl adenines. These compounds were further subjected to selective OXONE^®/alumina mediated oxidation followed by deprotection of the amine leading to the desired sulfoxides and sulfones.     

Synthesis of guanine from 3-methylxanthine

Summary A new preparative method of obtaining guanine from 3-methylxanthine has been developed.L. A. Gutorov and V. S. Aleksandrova are Deceased.Center for Drug Chemistry, All-Russian Scientific-Research Institute for Pharmaceutical Chemistry, Moscow 114815, State Institute for Blood Substitutes and Drugs, Moscow 109044. Zaporozhe State Medical Institute, Zaporozhe 330074. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 388–390, March, 1995.Original article submitted February 4, 1995.     

N1- and C6-substituted adenines: a regioselective and efficient synthesis

New and efficient methods for the synthesis of N1-substituted and C6-substitued adenines were developed from the easily accessible 5-aminoimidazole-4-carboxamidines. Condensation of these compounds with triethyl orthoformate led to the selective synthesis of the N1-substituted adenines. Regioselective preparation of C6-substituted adenines could be accomplished when the same precursors were combined with dimethylformamide diethyl acetal. These C6-substituted adenines could also be obtained from the N1-substituted adenines by Dimroth rearrangement in the presence of dimethyl amine.     

2-氰基-3-甲硫基-3-取代甲氨基丙烯酸酯类化合物的合成及其除草活性

A series of 2-cyano-3-methylthio-3-substituted methylaminoacrylates were synthesized as herbicidal inhibitors of photosystem Ⅱ （PSⅡ） electron transport, in order to estimate the effect of fluorine atom, pyridyl group, chirality and ester chain on activity. The important intermediate 2-fluoro-5-aminomethylpyridine was synthesized with high yield. The bioassay results showed that most of rifle compounds had high herbicidal activity in postemergence treatment. The introduction of an a-methyl into the 3-substituted methylamino could improve the activity notably. The replacement of hydrogen by chlorine or fluorine group and phenyl by pyridyl group showed different effects, and at the same time, the ester chain affected the activity too.     

Synthesis of N6-substituted adeninyl-9-β-D-glucofuranuronosides

N₆-substituted adeninyl-9--D-glucofuranuronosides have been obtained by the condensation of trimethylsilylated 6-aminopurines with 1,2,5-tri-O-acetyl-ß-d-glucofurano-6,3-lactone. The structure of the glucuronides was demonstrated by the UV, IR, and PMR spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 103–106, January, 1986.     

Synthesis of some N4-substituted isatin-3-thiosemicarbazones

In this article, we describe a simple and new method for the synthesis of some N4-substituted isatin-3-thiosemicarbazones based on the reactions of the common intermediate, methyl 2-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1-hydrazinecarbodithioate, prepared by condensing isatin with methyl 1-hydrazinecarbodithioate, and the readily available amines in essentially a one-step reaction. The synthesized thiosemicarbazones were fully characterized by their physical, analytical, and spectral (IR, 1H-NMR, EIMS) data.     

(3R,5R)-3,5-二羟基-6-取代己酸不对称合成研究进展

概述近 2 0年来 ( 3R ,5R) 3 ,5 二羟基 6 取代己酸不对称合成进展 ,并提出其研究方向 .     

Synthesis of N(1)-substituted 5-amino-3-methylpyrazoles

With the aim of preparing new biologically active compounds a series of N₍₁₎-substituted 5-amino-3-methylpyrazoles has been obtained from -aminocrotononitrile and mono-substituted hydrazines.K. A. Timiryazev Moscow Agricultural Academy, Moscow 127550, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, 342–344, March, 2000.     

3-芳氧基-6-取代哒嗪的合成及其除草活性

合成了系列3-芳氧基-6-取代哒嗪类化合物.化合物结构经¹HNMR、元素分析、IR和MS确证.生物活性测试结果表明,该类化合物具有很好的除草活性,讨论了其结构与除草活性的关系.     

Synthesis of N(3-dimethylaminopropyl)-6-substituted naphtho[2,1-b]thiophene-4-carboxamides

A series of N-(3-dimethylaminopropyl)-6-substituted naphtho[2,1-b]thiophenes-4-carboxamides have been synthesized. 6-Substituted naphtho[2,1-b]thiophene-4-carboxylic acids were obtained upon oxidative-photo-cyclization of α-(2-thienyl)-β-arylacrylic acids. The naphtho[2,1-b]thiophene carboxylic acids were converted to the corresponding amides through their acid chlorides or, in one case, by use of 1,1-carbonyldiimidazole coupling of the amine and the acid.     

Synthesis and molecular structure of 6-aryl-3-ethoxycarbonyl-4-hydroxypyridazines

EthylZ-5-aryl-2-diazo-5-hydroxy-3-oxopent-4-enoates interact with triphenylphosphine to give 6-aryl-3-ethoxycarbonyl-4-hydroxypyridazines (Ar=Ph, 4-MeC₆H₄, 4-ClC₆H₄). Quantum-chemical calculations (MNDO) were performed to estimate the tautomeric equilibrium in the latter using a 6-phenyl-substituted derivative as an example. Acetylation of the 4-hydroxypyridazines led to 4-acetoxy-6-aryl-3-ethoxycarbonylpyridazines. The structure of the latter was confirmed by an X-ray diffraction analysis of 4-acetoxy-3-ethoxycarbonyl-6-(p-tolyl)pyridazine. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2260–2263, December, 1997.     

Central depressant effects of N3-substituted 6-azauridines in mice.

Central depressant effects in mice of N3-substituted 6-azauridines (6-AzUd) (1) were examined by intracerebroventricular (i.c.v.) injection. Eleven derivatives including alkyl-, benzyl-, xylyl- and phenylethyl-substitution onto the N3-position of 1 were synthesized and their pharmacological effects were evaluated using hypnotic activity, locomotor activity, motor incoordination and pentobarbital-induced sleep prolongation as indices. Six of 12 compounds showed the hypnotic activity. At a dose of 2 mumol/mouse, the mean sleeping time induced by 1, N3-benzyl-6-AzUd (7), N3-o-xylyl-6-AzUd (8), N3-m-xylyl-6-AzUd (9), N3-p-xylyl-6-AzUd (10) and N3-alpha-phenylethyl-6-AzUd (11) was 14, 11, 45, 12, 9 and 16 min, respectively. These derivatives and N3-beta-phenylethyl-6-AzUd (12) (1.5 mumol/mouse) significantly prolonged pentobarbital-induced (40 mg/kg, i.p.) sleeping time, whereas none of the N3-alkylated derivatives (methyl-, ethyl-, n-propyl-, n-butyl- and allyl-substitution) exerted the hypnotic activity or pentobarbital-induced sleep prolongation. Nucleoside 1 and its xylyl-derivatives (1.5 mumol/mouse) significantly decreased locomotor activity of mice, their effects paralleled the hypnotic activity. These compounds (1.5 mumol/mouse) also produced motor incoordination and potentiated the effect of diazepam-induced motor incoordination. These results indicate that 1 and its benzyl-related derivatives, but not alkyl-derivatives have a depressant effect on the central nervous system.     

3－苯基－5－取代苯氨基－6－甲基－1，2，4－三嗪的合成

３－苯基－５－取代苯氨基－６－甲基－１，２，４－三嗪的合成陆忠娥，曾润生，席海涛（苏州大学化学系，苏州，２１５００６）关键词硫代苯甲酰胺，α－乙酰基硫代甲酰苯胺，Ｎ＇－氨基苯甲脒，３－苯基－５－取代苯氨基－６－甲基－１，２，４－三嗪１，２，４－三嗪类...     

Synthesis of α-substituted 3-ulosonic acids from aldonolactones

Zinc-silver/graphite mediated Reformatsky-reaction of furanoid aldonolactones with α-bromo-esters allows the synthesis of α-substituted 3-ulosonic acids in high yields.     

Synthesis of 3-substituted pyrrolidines

A method was developed for the synthesis of derivatives of 3-substituted pyrrolidines from activated alkenes by 1,3-dipolar cycloaddition of unstable 2-benzylazomethylide, generated in situ from N-benzyl-N-(methoxymethyl)-N-(trimethylsilyl)amine. A method was developed for the reduction of 4-(3-pyrrolidyl)pyridine, prepared by the above-mentioned method, to the corresponding derivatives of (3-pyrrolidyl)piperidine with high yields under mild conditions. Dedicated to E. J. Lukevics on his 70th birthday __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 41–48, January, 2007.     

Synthesis of 3-substituted furylethylamines

A method for the synthesis of the previously unknown 1-(3-furyl)ethylamine and [1-(3-furyl)ethyl]-N-methylamine was developed. The 3-furylcarbaldehyde was converted sequentially to 3-cyanofuran and then 3-acetylfuran. Reduction of the oxime or methylimine of 3-acetylfuran leads to the corresponding 3-substituted furylethylamines.M. V. Lomonosov Moscow State University, Moscow 119899, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 187–189, February, 1999.     

Synthesis of 3-substituted indazoles from arynes and N-tosylhydrazones

Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo compounds and arynes.     

Synthesis of CF3-substituted sulfoximines from sulfonimidoyl fluorides

N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert-Prakash reagent (TMSCF(3)) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.