Five-membered-ring-substituted 1-methyl-1H-indeno[1,2-b]pyridines

1-Methyl-1H-indeno[1,2-b]pyridine and 1-methyl-1H-5-(, -dicarbomethoxyvinyl)-(formyl, acetyl)indeno[3,2-b]pyridines were obtained by treatment of N-methyl-4-azafluorenium iodide, as well as mixtures of it with acetylenedicarboxylic ester, dimethylformamide (DMF), and phosphorus oxychloride or acetic anhydride, with bases. 4-Azafluoronenone was used to synthesize 9-(p-methoxyphenyl)-4-azafluoren-9-ol, which was reduced to 9-(p-methoxyphenyl)-4-azafluorene, and 1-methyl-1H-5-(p-methoxyphenyl)indeno[3,2-b]pyridine was obtained from the methiodide of the latter.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1382–1386, October, 1981.     

1,4-Dihydropyridine-3,5-di-and 2-methyl-4-aryl-5-oxo-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carbothionic acid ethyl esters

Methods for the synthesis of 1,4-dihydropyridine-3,5-di- and 4-aryl-5-oxo-4,5-dlhydro-1H-indeno[1,2-b]pyridine-3-carbothionic acid ethyl esters were developed. A comparative analysis of the physicochemical characteristics of this series of substances is given.Their reactivities in electrochemical and chemical oxidation reactions were studied. The electrochemical oxidation potentials of the thionic acid esters are found in a lower anodic range as compared with their oxygen analogs. According to the ionization constants, the thionic acid esters of 4,5-dihydroindenopyridines are stronger acids than the carbonyl esters; this is explained by participation of the free 3d orbitals of the sulfur atom in stabilization of the anion.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.2, pp. 210–216, February, 1984.     

Structure and properties of 2,4a-dimethyl-4-phenyl-3-ethoxycarbonyl-5-oxo-4a,5-dihydro-4H-indeno[1,2-b]pyridine

The molecular and crystal structure of 2,3a-dimethyl-4-phenyl-3-ethoxycarbony-5-oxo-4a,5-dihydro-4H-indeno[1,2-b]pyridine has been determined, and its reduction and alkaline and acid hydrolysis reactions have been studied.Translated from Khimiya Geterotsiklicheskikh Soedineii, No. 10, pp. 1388–1392, October, 1984.     

新型5H-茚[1,2-b]吡啶和11H-茚[1,2-b]喹啉三氟甲磺酸盐衍生物的合成其及抗肿瘤活性

以1-茚酮为原料,设计并合成了新化合物1-甲基-5-(4-二甲氨基苄烯)-5H-茚[1,2-b]吡啶三氟甲磺酸盐(5a)和5-甲基-11-(4-二甲氨基苄烯)-11H-茚[1,2-b]喹啉三氟甲磺酸盐(5b),其结构经NMR,IR和MS表征。采用MTT法,以HEP-2和K562为测试肿瘤细胞株对5a和5b进行抗肿瘤活性检测,结果显示其有良好的抗肿瘤活性。     

Synthesis of 5-phenyl-2,3,8,9-tetramethoxy-11H-indeno[1,2-c]isoquinoline

A novel approach to the title compound 10 starting with a conveniently available cinnamic acid is proposed. It involves a Friedel-Crafts reaction followed by the synthesis of the amide and subsequent cyclodehydration via a Bischler-Napieralski reaction.     

Interactions of lysozyme with 6-amino-4-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles: a fluorescence quenching study.

The interactions between 6-amino-4-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and lysozyme (LYSO) were investigated by using tryptophane fluorescence quenching and 6-amino-4-(2-hydroxyphenyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (1) was studied in detail because of its high water solubility. At different temperatures, the quenching constants K(SV), the binding constants K and the binding sites n of LYSO with 1 were determined and the thermodynamic parameters were calculated. The distance r between tryptophane residues and 1 was obtained according to the Forster mechanism of non-radiation energy transfer. Furthermore, synchronous fluorescence spectroscopy data indicated that the association between 1 and LYSO changed LYSO's conformation and that the hydrophobic interaction played a major role in 1-LYSO association. It was proved that the fluorescence quenching of LYSO by 1 was related to the formation of a 1-LYSO complex and to a non-radiation energy transfer.     

一锅法合成新型7-苯基-10-芳基-5H-茚并[1,2-b]喹啉-9,11-二酮类化合物

以1,3-茚二酮,5-苯基-1,3-环己二酮和芳醛为原料,脯氨酸为催化剂,经"一锅法"合成了5个新型的7-苯基-10-芳基-5H-茚并[1,2-b]喹啉-9,11-二酮化合物,收率73%~80%,其结构经1H NMR,ESI-MS和元素分析表征。     

微波辐射下一锅法合成2-氨基-6-溴-4-芳基-5H-茚并[1,2-b]吡啶-3-腈衍生物

以芳香醛、4-溴茚酮、丙二腈和醋酸铵为原料,分别用微波辐射和传统加热法,一步法合成7种未见文献报道的2-氨基-6-溴基-4-芳基-5H-茚并[1,2-b]吡啶-3-腈衍生物.对比两种方法,在常压下微波具有反应时间短、产率较高等特点.所有化合物均经IR,1HNMR和元素分析确定.     

Convenient Ultrasound-Promoted Regioselective Synthesis of Fused 6-Amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

A multicomponent, catalyst-free reaction for the synthesis of fused 6-amino-3-methyl-4-aryl-1H-pyrazolo [3,4-b] pyridine-5-carbonitrile from 3-amino-5-methylpyrazole, malononitrile, and substituted aldehydes under ultrasound irradiation in short reaction times (8–10 min) with good yields (85–98%) is reported.

Synthesis of 3-phenyl- and 3-phenyl-1-methylimidazo [5, 1-b] benzoxazoles

Reduction of 2-benzoylbenzoxazole oxime gives 2-(-aminobenzyl) benzoxazole, converted to the formyl or acetyl derivative by treatment with, respectively, ethyl formate or acetic anhydride. Thiourea derivatives are obtained by treating 2-(-aminobenzyl) benzoxazole with arylisothiocyanates. Heating the above formyl or acetyl derivative with phosphorus oxychloride converts them to 3-phenyl- and 3-phenyl-1-methylimidazo [5, 1-b]-benzoxazole, which are representative members of a new tricyclic system. It did not prove possible to cyclize 1-[-(benzoxazolyl-2) benzyl]-3-phenylthiourea.     

Recovery of plutonium from oxalate supernatant using 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone

Summary Extraction of Pu(IV) from oxalate supernatant was carried out employing 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) in xylene as extractant. The conditions for quantitative extraction were determined by the variation of ligand, oxalic acid and nitric acid concentration. Quantitative stripping was achieved using a mixture of 0.4M oxalic acid and 0.4M ammonium oxalate. Extraction of Pu(IV) from synthetic oxalate supernatant solution containing 3M nitric acid and 0.2M oxalic acid was investigated under various loading conditions employing 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone in xylene as extractant. Under uranium loading conditions the Pu extraction decreased significantly while with increased Pu loading whereas the D_Pu value was influenced marginally. The effect of a redox reagent on Pu extraction was also investigated.     

Synthesis of 3-alkoxycarbonylaminomethylcarbonylamino-4-benzoyl-1,2-dihydropyridines and their cyclization to 5-phenyl-1,3,8,9-tetrahydro-2H-pyrido[3,4-e]-1,4-diazepin-2-ones

The regiospecific reaction of 3-benzyloxycarbonylaminomethylcarbonylamino-4-benzoylpyridine (6a) , or 3-t-butoxycarbonylaminomethylcarbonylamino-4-benzoylpyridine (6b) , with either acetyl chloride or ethyl chloroformate, and either n-butylmagnesium chloride or phenylmagnesium bromide afforded the respective 1-acetyl (or ethoxycarbonyl)-2-n-butyl (or phenyl)-3-benzyloxy (or t-butoxy) carbonylaminomethylcarbonylami-no-4-benzoyl-1,2-dihydropyridines 7 in 60-75% yield. Reaction of 1-acetyl (or ethoxycarbonyl)-2-n-butyl (or phenyl)-3-t-butoxycarbonylaminomethylcarbonyl-4-benzoyl-1,2-dihydropyridines 7b, 7f, 7d, 7h with trifluoroacetic acid gave the corresponding 5-phenyl-8-acetyl (or ethoxycarbonyl)-9-n-butyl (or phenyl)-1,3,8,9-tetrahydro-2H-pyrido[3,4-e]-1,4-diazepin-2-ones 8a, 8b, 8c, 8d respectively in 45–63% yield. N¹-Methylation of 5-phenyl-8-acetyl-9-n-butyl (or phenyl)-1,3,8,9-tetrahydro-2H-pyrido[3,4-e]-1,4-diazepin-2-ones 8a, 8b using sodium hydride and iodomethane yielded the corresponding N¹-methyl derivatives 9a (48%) and 9b (54%). Oxidation of 5,9-diphenyl-8-ethoxycarbonyl-1,3,8,9-tetrahydro-2H-pyrido[3,4-e]-1,4-diazepin-2-one (8d) using p-chloranil afforded 1,3-dihydro-5,9-diphenyl-2H-pyrido[3,4-e]-1,4-diazepin-2-one (10) . 5-Phenyl-8-acetyl-9-n-butyl-1,3,8,9-tetrahydro-2H-pyrido[3,4-e]-1,4-diazepin-2-one (8a) and the corresponding 8-ethoxycarbonyl analog 8c exhibited weak anticonvulsant activity indicating that 8a and 8c may be acting at the same site as the 7-halo-1,4-benzodiazepin-2-one class of compounds.     

Formation of alkyl 1-methyl-3,9-dioxo-2-phenyl-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]quinoline-1-carboxylates by thermolysis of alkyl 1,5-diaryl-4-methyl-2,3,6-trioxo-1,2,3,4,5,6-hexahydropyrrolo[3,4-b]pyrrole-4-carboxylates

Russian Journal of Organic Chemistry -