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1.
Yoshinori Tominaga Lyle W. Castle Raymond N. Castle 《Journal of heterocyclic chemistry》1996,33(4):1319-1321
Photocyclization of the substituted 2-([1]benzothien-3-yl)-3-phenylpropenoic acids 3a-c in the presence of iodine and air in a benzene-cyclohexane mixture afforded a separable mixture of three compounds, benzo[b]naphtho[2,1-d]thiophene-6-carboxylic acids 4a-c , 6H-benzo[b]naphtho[2,3-d]thiopyran-6-ones 5a-c , and 10-methoxy-2-methyl-6H-benzo[b]naphtho[2,3-d]pyran-6-one ( 6 ). 相似文献
2.
Belskaya N. P. Koksharov A. V. Deryabina T. G. Eltsov O. S. Slepukhin P. A. Bakulev V. A. 《Russian Chemical Bulletin》2010,59(4):833-837
Reactions of 2-arylazo-3-(1-azacycloalk-1-yl)-3-methylsulfanylacrylonitriles with male-imide in benzene gave octahydropyrrolo[3,4-a]pyrrolizines 2a–c, decahydro-2,7a-diaza-cyclopenta[a]indene 2e, and decahydro-5-oxa-2,7a-diazacyclopenta[a]indene 2f as a result of 1,3-dipolar cycloaddition. In a similar reaction with 3-allylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles
3, dipolar cycloaddition and intramolecular cyclization competed to give a mixture of compounds 2 (major products) and 1,4,6,7,8,8a-hexahydropyrrolo[2,1-c]-1,2,4-triazines 4b–d, 1,6,7,8,9,9a-hexahydro-4H-pyrido[2,1-c]-1,2,4-triazine 4e, and 1,4,6,7,9,9a-hexahydro-1,4-oxazino[3,4-c]-1,2,4-triazine 4f (minor products). 相似文献
3.
The synthesis of benzo[b]phenanthro[1,2-d]thiphene ( 1 ), benzo[b]phenanthro[4,3-d]thiophene ( 2 ), benzo-[b]phenanthro[2,1-d]thiophene ( 3 ) and benzo[b]phenanthro[3,4-d]thiophene ( 4 ) from appropriately substituted olefines by photochemical cyclodehydrogenation is described. The photolysis of olefin 9 gave a mixture of 4 and anthra[1,2-b]benzo[d]thiophene ( 5 ). 相似文献
4.
Yoshifumi Watanabe Hirotaka Yoshiwara Munefumi Kanao 《Journal of heterocyclic chemistry》1993,30(2):445-451
The syntheses of 4-(benzo[b]furan-3-yl)piperidines, 4-(benzo[b]furan-2-yl)piperidines and 4-(benzo[b]thiophen-3-yl)piperidines with 5-HT2 antagonist activity are described. Reaction of 1-acetyl-4-(2,4-difluorobenzo-yl)piperidine 2 with methyl glycolate gave methyl 6-fluoro-3-(1-acetylpiperidin-4-yl)benzo[b]furan-2-carboxylate 3 , which was converted to 2-[2-[4-(benzo[b]furan-3-yi)piperidin-1-yl]ethyl-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyridin-3(2H)-one hydrochloride 9 . Analogous benzo[b]furans 17a-d and benzo[b]thiophenes 10a,b and 18a were prepared by a similar method. Cyclization of 4-fluoro-2-(4-pyridinylmethoxy)acetophenones 20a,b afforded 4-(benzo[b]furan-2-yl)pyridines 21a,b , which were converted to 2-[2-[4-(benzo[b]furan-2-yl)-piperidin-1-yl]ethyl-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochlorides 24a,b. Among them, benzo[b]furans 9 and 17a,d and benzo[b]thiophenes 10 and 18a showed potent 5-HT2 antagonist activity in vitro. 相似文献
5.
E. A. Kaigorodova A. A. Osipova L. D. Konyushkin G. D. Krapivin 《Russian Chemical Bulletin》2004,53(4):853-859
Reactions of 2,5-dimethoxytetrahydrofuran with 3-aminothieno[2,3-b]pyridines afford a number of substituted 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines. The possibility of the reaction and the yield of the product are determined by the character of a substituent in position 2 of thieno[2,3-b]pyridine. The Curtius rearrangement of 2-acylazido-3(1H-pyrrol-1-yl)thieno[2,3-b]pyridines yields 4,5-dihydropyrido[3",2":4,5]thieno[2,3-e]pyrrolo[1,2-a]pyrazin-4-ones. The molecular and crystal structures of ethyl 4-methoxymethyl-6-methyl-3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridine-2-carboxylate were determined by X-ray diffraction analysis. 相似文献
6.
N-Phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines (6a-q) have been synthesized by the Hantzsch thiazole reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones (4a-e) with suitably substituted thioureas using microwave heating. The ethanones (4a-e) were prepared by the reaction of 6-phenylimidazo[2,1-b]thiazoles (3a-e) with chloroacetylchloride in refluxing 1,4-dioxane whereas the thiazoles (3a-e) were synthesized by the reaction of 2-bromo-1-phenylethanones (2a-e) with thiazol-2-amine in refluxing acetone. 相似文献
7.
Yuh-Wen Ho 《中国化学会会志》1999,46(6):955-962
Coupling the diazonium salt of 3-amino-2-cyano-4,6-dimethylthieno[2,3-b]pyridine 1 with malononitrile 2 gave 2-cyano-3-(hydrazonomalononitrile)-4,6-dimethylthieno[2,3-b]pyridine 3 which then reacted with hydrazine compounds 4a-4h to yield corresponding 2-cyano-3-(3,5-diamino-1-substituted-pyrazol-4-yl)azo-4,6-dimethylthieno[2,3-b]pyridines 5a-5h. The 2-cyano-3-(2-amino-5,7-disubstituted-pyrazolo-[1,5-a]pyrimidine-3-yl)azo-4,6-dimethylthieno[2,3-b]pyridines 7a-7f were obtained in good yield by the cyclocondensation reaction of 2-cyano-3-(3,5-diamino-pyrazol-4-yl)azo-4,6-dimethylthieno[2,3-b]pyridine 5a with the appropriate 1,3-diketones 6a-6f under acidic condition. 相似文献
8.
Yuh-Wen Ho 《中国化学会会志》1999,46(1):91-96
The reaction of 3-amino-4,6-dimethyl-2-thieno[2,3-b]pyridine carbohydrazide ( 1 ) with appropriate chalcones 2a-2d in the presence of acid catalyst produced the corresponding 3-amino-2-[(3,5-disubstituted-pyrazolin-1-yl)carbonyl]-4,6-dimethylthieno[2,3-b]pyridines 3a-3d . 3-Amino-2-[(3-substituted-pyrazolin-1-yl)carbonyl]-4,6-dimethylthieno[2,3-b]pyridines 7a, 7b were also obtained by the cyclization reaction of carbohydrazide 1 with Mannich base derivatives 6a, 6b under basic condition. 相似文献
9.
Nuray Ulusoy Muammer Kiraz Ömer Küçükbasmacı 《Monatshefte für Chemie / Chemical Monthly》2002,133(10):1305-1315
Summary. New 4-alkyl/aryl-1-((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-3-thiosemicarbazides and 3-alkyl/aryl-2-(((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinones were synthesized from 6-(4-bromophenyl)-imidazo[2,1-b]thiazole-3-acetic acid hydrazide. Their structures were elucidated by elemental analyses and spectroscopic data. All compounds
were tested for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by the
microbroth dilution technique. The compounds were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294); they exhibited varying degrees of inhibition in the in vitro primary screening at 6.25 μg · cm−3. The most active compound was 3-(4-nitrophenyl)-2-(((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinone.
Corresponding author. E-mail: nurayulusoy@yahoo.com
Received December 10, 2001. Accepted (revised) March 1, 2002 相似文献
10.
Nuray Ulusoy Muammer Kiraz ?mer Kü?ükbasmac? 《Monatshefte für Chemie / Chemical Monthly》2002,20(3):1305-1315
New 4-alkyl/aryl-1-((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-3-thiosemicarbazides and 3-alkyl/aryl-2-(((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinones were synthesized from 6-(4-bromophenyl)-imidazo[2,1-b]thiazole-3-acetic acid hydrazide. Their structures were elucidated by elemental analyses and spectroscopic data. All compounds were tested for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by the microbroth dilution technique. The compounds were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294); they exhibited varying degrees of inhibition in the in vitro primary screening at 6.25 μg · cm−3. The most active compound was 3-(4-nitrophenyl)-2-(((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinone. 相似文献
11.
W. David Cotterill Muhammad Iqbal Robert Livingstone Maurice V. Walshaw 《Journal of heterocyclic chemistry》1974,11(3):283-286
The reaction between 3,3-bis(methoxyphenyl)-3H-naphtho[2,1-b]pyran and 1,3-bis(methoxyphenyl)-1H-naphtho[2,1-b]pyran under acid conditions gives a 7a,15a-dihydro-7a,15-bis(methoxyphenyl)-16-[2,2-bis(methoxyphenyl)-l-vinyl]dinaphtho-[2,1-b:2,1-g]-4H,5H-pyrano[2,3-b]-pyran. 相似文献
12.
O. V. Surikova Z. G. Aliev A. G. Mikhailovskii 《Chemistry of Heterocyclic Compounds》2008,44(12):1500-1504
2,3-Dioxpyrrolo[2,1-a]isoquinolines react with 1,8-naphthalenediamine in 2-propanol in the presence of p-toluenesulfonic acid to give 2-spiro-(1,2-dihydroperimid-2-yl)-5,5-dialkyl-2,3,5,6-tetrahydro-pyrrolo[2,1-a]isoquinolin-3-ones whose structure was confirmed by X-ray analysis.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1849–1854, December, 2008. 相似文献
13.
V. B. Sokolov A. Yu. Aksinenko I. V. Martynov 《Russian Journal of General Chemistry》2014,84(1):86-88
Cyclocondensation of methyl 2-(5-methylisoxazol-3-yl)imino-3,3,3-trifluoropropionate with 1,3-binucleophiles such as benzamidines, aminothiazoline, and 2-aminocrotonic acid nitrile results in trifluoromethyl-containing 3,5-dihydro-4-ones, 2,3-dihydro-6H-imidazo[2,1-b]thiazol-5-one, and 4,5-dihydro-1H-pyrrole-3-carbonitrile. 相似文献
14.
Yuh-Wen Ho 《中国化学会会志》1999,46(6):947-953
The reaction of 3-amino-4,6-dimethyl-2-thieno[2,3-b]pyridine carbohydrazide ( 1 ) with appropriate 1,3-diketones 2a-2d in glacial acetic acid afforded 3-amino-2-[(3,5-disubstituted-pyrazo)-1-yl)carbonyl]-4,6-dimethylthieno[2,3-b]pyridines 3a-3d. 3-Amino-2-[(5-amino-3,4-disubstituted-pyrazol-1-yl)carbonyl]-4,6-dimethylthieno[2,3-b]pyridines 5a-5h were also prepared by treatment of carbohydrazide 1 with appropriate alkylethoxymethylenes and ketene dithioacetals 4a-4h , respectively. 相似文献
15.
Masatomo Iwao Milton L. Lee Raymond N. Castle 《Journal of heterocyclic chemistry》1980,17(6):1259-1264
All isomers of the parent phenanthro[b]thiophenes, namely, phenanthro[1,2-b]thiophene, phenanthro-[2,1-b]thiophene, phenanthro[2,3-b]thiophene, phenanthro[3,4-b]thiophene, phenanthro[3,4-b]thiophene, phenanthro[4,3-b]thiophene and phenanthro[9,10-b]thiophene have been synthesized. 相似文献
16.
Yasuyoshi Miki Noriko Nakamura Hiroko Hachiken Shoji Takemura 《Journal of heterocyclic chemistry》1989,26(6):1739-1745
Treatment of 3-(hydroxymethyl)pyrazolo[1,5-a]pyridines with trifluoroacetic acid in refluxing dichloro-methane led to the formation of bis(pyrazolo[1,5-a]pyrid-3-yl)methanes or bis[(pyrazolo[1,5-a]pyrid-3-yl)]-methyl ethers depending upon the concentration of trifluoroacetic acid. In contrast, similar treatment of 3-(1-hydroxyethyl)pyrazolo[1,5-a]pyridines gave a mixture of 3-vinylpyrazolo[1,5-a]pyridines and 1,3-bis(pyrazolo-[1,5-a]pyrid-3-yl)-1-butenes. 相似文献
17.
Pechkin A. A. El'chaninov M. M. Stoyanov V. M. 《Russian Journal of Organic Chemistry》2002,38(5):726-730
Condensation of 9,10-phenanthrenequinone with 2-furaldehyde and 2-thiophenecarbaldehyde in glacial acetic acid in the presence of ammonium acetate gave 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles which were converted into the corresponding 1-methyl derivatives. The furan and thiophene rings in the products lose their acidophobic properties. Depending on the conditions, electrophilic substitution reactions in 2-(2-furyl)- and 2-(2-thienyl)phenanthro[9,10-d]imidazoles occur both at the furan (thiophene) and phenanthrene moieties. 相似文献
18.
Marvin L. Tedjamulia Yoshinori Tominaga Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1983,20(4):861-866
The synthesis of benzo[b]phenanthro[2, 3-d]thiophene ( 5 ), benzo[b]phenanthro[4, 3-d]thiophene ( 6 ), benzo-[b]phenanthro[2, 1-d]thiophene ( 9 ), benzo[b]phenanthro[3, 2-d]thiophene ( 14a ), anthra[1, 2-b]benzo[d]thiophene ( 24 ), anthra[2, 3-b]benzo[d]thiophene ( 29 ) and anthra[2, 1-b]benzo[d]thiophene ( 30 ) is described as well as the preparation of 13-methylbenzo[b]phenanthro[3, 2-d]thiophene ( 14b ). 相似文献
19.
Hirotaka Kudo Marvin L. Tedjamulia Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1984,21(6):1833-1839
The synthesis of phenanthro[1,2-c]dibenzothiophene (6) , phenanthro[4,3-c]dibenzothiophene (10) , phenanthro[2,1-a]dibenzothiophene (14) , phenanthro[3,4-a]dibenzothiophene (16) , phenanthro[1,2-a]dibenzothiophene (19) , phenanthro[2,1-b]dibenzothiophene (20) , 8-methylphenanthro[3,2-a]dibenzothiophene (24) , 7-methylphenanthro[1,2-a]dibenzothiophene (25) , phenanthro[3,4-a]dibenzothiophene (27) , phenanthro[4,3-a]-dibenzothiophene (28) , 6-methylphenanthro[2,3-a]dibenzothiophene (31) , and 5-methylphenanthro[4,3-a]dibenzothiophene (32) is described. 相似文献
20.
L. H. Klemm Michael P. Stevens Long K. Iran John Sheley 《Journal of heterocyclic chemistry》1988,25(4):1111-1116
Regioselectivity occurs in the sulfur-bridging reactions of 2,2′-binaphthyl (1) and 1-(2-naphthyl)cyclohexene (7) by means of hydrogen sulfide and a chromia-alumina-magnesia catalyst (designated I) in a flow apparatus at 550°. Thus, 1 gives a higher yield (6.1%) of dinaphtho[1,2–6:2′,l'-d]thiophene from 1,1′-bridging than of dinaphtho[1,2-b:2′,3′-d]thiophene (3.4%) from l,3′-bridging. No product expected from 3,3′-bridging was identified. Substrate 7 undergoes both dehydrogenation and bridging to yield 2-phenylnaphthalene (8%), benzo[b]naphtho[2,1-d]thiophene (9%) from alpha bridging, and benzo[b]naphtho[2,3-d]thiophene (3%) from beta bridging into the naphthalene ring. Exploratory studies showed that either sulfided catalyst I or a sulfided molybdenum( VI ) oxide-alumina-cobalt( II ) oxide catalyst ( II ) effects hydrodehalogenation of various monohalo- and polyhaloarenes (where halo, X, is chloro or bromo) at 450–550°. In the biphenyl, phenanthrene, naphthalene, and pyrene systems, halogen was lost either under sulfur-bridging conditions or under hydrogenolysis conditions, i.e. with methanol as a reactant. For every substrate the parent arene was isolated or identified as a reaction product. In selected experiments, acid HX was also identified in the effluent. Use of hydrogen sulfide as a reactant led to formation of dibenzothiophene and phenanthro[4,5-bcd]thiophene as main products in the biphenyl and phenanthrene systems, respectively; while use of methanol as a reactant gave small amounts of methyl bromide (for X = Br) and methylarenes. 相似文献