Furylcyclohexenones. 3. Synthesis and properties of 6-acetyl-3(5)-furylcyclohex-2-enones. Molecular and crystal structure of 6-acetyl-3-(2-furyl)-5-phenylcyclohex-2-enone

6-Acetyl-3(5)-furylcyclohex-2-enones were prepared by condensation of furan-containing chalcones with acetylacetone. Acetylcyclohex-2-enones were subjected to C-methylation. Studies by IR and ¹H NMR spectroscopy demonstrated that the resulting compounds occur predominantly in the enol form both in solutions and in the crystalline state. The molecular structure of 6-acetyl-3-(2-furyl)-5-phenylcyclohex-2-enone was established by X-ray diffraction analysis.     

Molecular and crystal structure of 4-acetyl-3-(5-nitrofurfuryl)-1-(4-chlorobenzylidene)-thiosemicarbazide

Krasnodarsk Polytechnical Institute. Translated from Zhurnal Strukturnoi Khimii, Vol. 33, No. 3, pp. 149–151, May–June, 1992.     

Synthesis and reactions of 3-acetyl-6-methyl-2-(methylthio)pyridine

A reaction of methyllithium with 3-cyano-6-methylpyridine-2(1 H)-thione followed by alkylation of the resulting 3-acetylpyridinethione, or a direct reaction of methyllithium with 3-cyano-6-methyl-2-(methylthio)pyridine, afforded 3-acetyl-6-methyl-2-(methylthio)pyridine. The ketone obtained was examined in bromination reactions under various conditions. Bromi-nation in methanol or chloroform, proceeding through the formation of sulfonium bromides, gave substituted 3-(bromoacetyl)pyridine. A reaction of 3-acetyl-6-methyl-2-(methyl-thio)pyridine with N-bromosuccinimide in CCl4 afforded N-(pyridinesulfenyl)succinimide. The bromo ketone was used for the synthesis of various heterocyclic compounds.     

Synthesis of 3-R2-4-R1-acetyl-(ethoxycarbonyl)-6-hydroxy-6-methylindazoles

It was discovered that functionally substituted tetrahydroindazoles can be aromatized by the action of sulfur. Previously unknown 3-R²-4-R¹-5-acetyl(ethoxycarbonyl)-6-methylindazoles were obtained. The products from aromatization cannot be obtained if a nitro group is introduced or one heteroatom in the substrate is replaced by oxygen.N. G. Chernyshevskii Saratov State University, Saratov, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 757–759, June, 1999.     

An efficient chiral synthesis of (R)-N-[3-acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)phenyl]-butanamide with high enantioselectivity

R-Enantiomer of the β-receptor antagonist N-[3-acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)phenyl] butanamide with high enantioselectivity was synthesized from cheap starting materials and enantiopure chiral reagent through an efficient,convenient and practical synthetic strategy.Title product was detected by 1H NMR,13C NMR,and MS,and the enatiomeric excess was determined by chiral HPLC analysis using a chiracel AD-H column.     

New synthesis of 2-aryl-3-hydroxy(alkoxy)-4-quinolones by ring expansion of 1-acetyl-2-arylmethylene-3-indolinones

Translated from Khimiya Geterotsiklicheskikh Soedinenii,'No. 2, pp. 279–280, February, 1992.     

Study of the azo-coupling of 6-hydroxy(methoxy)-2-phenyl-3-hydroxypyridines

Russian Chemical Bulletin -     

Acylation of 2-azahetarylacetonitriles with (acetylthio)acetyl and α-(acetylthio)-propionyl chlorides. Production of 5-amino-4-hetarylthiophen-3(2H)-ones

3-Cyano-3-hetaryl-2-oxopropyl-and 3-cyano-3-hetaryl-1-methyl-2-oxopropyl ethanethioates were obtained by the acylation of 2-azahetarylacetonitriles with (acetylthio)acetyl and α-(acetylthio)propionyl chlorides respectively. They are deacetylated by the action of amines and undergo cyclization with the formation of 5-amino-4-hetarylthiophen-2(2H)-ones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1314–1319, September, 2006.     

Molecular and crystal structure of 3-(p-tolylamino)-propionitrile

Conclusions Crystalline 3-(p-tolylamino)propionitrile has trans conformation for the Ar-N-C-C fragment and gauche conformation for the N-C-C-CN fragment. The deviation of the aniline fragment from planarity is 23.6°.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2481–2483, November, 1987.     

Crystal and molecular structure of [9-(2′-tosylaminophenyl)-6-methylthio-3-acetyl-5,7,8-triazanone-3,6,8-thien-2-one]

Institute for Applied Physics, Academy of Sciences of the Moldavian SSR. Institute of Chemistry, Academy of Sciences of the Moldavian SSR. Nat. Research Institute for Physics and Organic Chemistry, Rostov State University. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 2, pp. 199–202, 1990.     

Reaction of 3-0-acetyl-14-anhydrodigitoxigenia and 3-0-acetyldigitoxigenin with osmium tetroxide

Treatment of 3-O-acetyl-14-anhydrodigitoxigenin ( 1 ) with 1.1 equivalents of OsO₄ gave both the 14α, 15α-diol 2 and the 14β, 15β-diol 4. Degradation to the corresponding methyl etianates 7 and 10 , respectively, established their stereochemistry. Treatment of both the 14-hydroxy-15-acetoxy-cardenolides 3 and 5 with OsO₄ leads to the expected mixtures of 20, 22-diols, a partial separation of which was achieved after acetylation. The butenolide ring of 3-O-acetyl-digitoxigenin ( 25 ) also reacted with OsO₄, yielding the two 20,22diols 26 and 27 , the stereochemistry of which has tentatively been assigned on the basis of NMR. data.     

新型4-N-(二茂铁亚甲基)-6-甲硫基-3-乙基-3-己醇手性配体的合成

以L-甲硫氨酸为手性源,经酯化、缩合、还原氨化及格氏试剂反应,设计并合成了一种新型的含硫二茂铁基的β-氨基醇手性配体--4-N-(二茂铁亚甲基)-6-甲硫基-3-乙基-3-己醇,其结构经<'1>H NMR,<'13>C NMR,IR及HR-MS表征.     

糖苷合成研究(ⅩⅩⅠ)2-N-(β-D-吡喃葡萄糖-1-基)-6-(4-卤代苯基)-3-哒嗪酮的合成

在相转移催化条件下,2,3,4,6-四-O-乙酰基-1-溴-1-脱氧-α-D-吡喃葡萄糖1与6-(4-卤代苯基)-3(2H)-哒嗪酮2反应,合成了4种新的哒嗪酮葡萄糖苷3;然后用干燥的氨气在0～-5 ℃下处理,得相应的2-N-(β-D-吡喃葡萄糖-1-基)-6-(4-卤代苯基)-3-哒嗪酮4. 这些化合物的结构经IR、1H NMR、13C NMR及元素分析所证实.     

Crystal structure of N-(3-nitrocinnamoyl)-N-(2-chlorophenyl)hydroxylamine

All-Union Scientific-Research Institute of Chemical Reagents and Specially Pure Chemicals. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 5, pp. 161–164, September–October, 1990.     

3-乙酰基-2-芳基-5-(6-吲哚基)-1,3,4-噁二唑啉化合物的微波合成及表征

噁二唑啉化合物由于具有杀虫[1],杀菌[2],抗艾滋病毒[3]等生物活性受到药物化学家的广泛关注.而吲哚因独特的化学结构使其衍生出的化合物显示出重要的生物活性,如抗疟疾[4]、抗肿瘤[5]、抗糖尿病[6]等,可以用作HT受体抑制剂[7]、环氧酶抑制剂[8]等.鉴于不同活性的基团在同一分子中聚集能明显改善化合物的生物活性这一特性,本文将吲哚引入到噁二唑啉化合物中,以期实现活性的叠加,从而发现新的生物活性更好的化合物.