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1.
Takaaki Horaguchi Hiroto Kobayashi Kazuhiro Miyazawa Eietsu Hasegawa Takahachi Shimizu Tsuneo Suzuki Kiyoshi Tanemura 《Journal of heterocyclic chemistry》1990,27(4):935-940
Tetrahydrocyclohepta[cd]benzofurans 7a-e were synthesized by the treatment of ( 5 -oxo-tetrahydro-5H-benzocyclohepten-4-yloxy)acetic acids 5a-e with sodium acetate in acetic anhydride or by heating of their esters 6a-e with sodium hydroxide or sodium hydride in dioxane. The yield of furans 7 decreased as a substituent R of acids 5 or esters 6 was changed from hydrogen to a methyl, ethyl, or isopropyl group. When R was a phenyl group furan 7e was always prepared in good yield. Sodium hydride was a useful base for synthesis of tetrahydrocyclohepta[cd]benzofurans. 相似文献
2.
Takaaki Horaguchi Eietsu Hasegawa Takahachi Shimizu Kiyoshi Tanemura Tsuneo Suzuki 《Journal of heterocyclic chemistry》1989,26(2):365-369
Cyclohepta[cd]benzofuran 2 was synthesized by heating (5-oxo-5H-benzocyclohepten-4-yloxy)acetic acid 16 with sodium acetate in acetic anhydride or by photocyclization of 16 in acetonitrile. Several reactions of cyclohepta[cd]benzofuran 2 were examined. Protonation of 2 with trifluoroacetic acid occurred at the 2-position to give a tropylium ion 17 . Catalytic hydrogenation of 2 with palladium on charcoal proceeded smoothly to give tetrahydrocyclohepta[cd]benzofuran 18 . The Diels-Alder reaction of 2 with tetracyano-ethylene produced an adduct 19 . Formylation of 2 with phosphorus oxychloride and dimethylformamide occurred easily at the 2-position to afford compound 20 . Cyclohepta[cd]benzofuran 2 has both properties of heptafulvene and benzofuran. 相似文献
3.
Ren-Hao Jin Bing-Zhu Yin Zhong-Tian Jin Kimiaki Imafuku 《Journal of heterocyclic chemistry》1990,27(3):583-586
3-Isopropenyltropolones 1a-c were treated with bromine in carbon tetrachloride to give 3-methyl-8H-cyclohepta[b]furan-8-ones 2a-c and their corresponding 7-bromo-substituted compounds 3a-c , while reactions in acetic acid gave the bromo-substituted compounds 3a-c . On the other hand, bromination of 1a-c with N-bromosuccinimide afforded 7-bromo-3-(2-bromo-1-methylethenyl)tropolones 5a-c . The compound 2a was treated with bromine to give 2-bromo-3-methyl-8H-cyclohepta[b]furan-8-one ( 4 ). The tropolones 5a-c were heated in the presence of potassium carbonate to give the cyclized compounds 3a-c . 相似文献
4.
Takaaki Horaguchi Takuji Kubo Kiyoshi Tanemura Tsuneo Suzuki 《Journal of heterocyclic chemistry》1998,35(3):649-653
Cyclohepta[cd]benzothiophene 3 , a new heterocyle, was synthesized starting from benzothiophene via eight steps in 14% total yield. Chemical reactions of 3 were examined on formylation, acetylation, bromination, catalytic hydrogenation and Diels-Alder reactions. The results show that the benzothiophene moiety of 3 has aromatic character and the carbon?carbon double bonds in a seven-membered ring posseses alkene-1ike character. 相似文献
5.
Kamal F. Atta Abdel Moneim El-Massry Hamida Abdel Hamid El Sayed H. El Ashry Adel Amer 《Journal of heterocyclic chemistry》1994,31(2):549-552
The transformation of 2-chloro-3-[5-(acetoxymethyl)-1-phenylpyrazol-3-yl]quinoxaline 3 to 1-aryl-4-[5-(hydroxymethyl-1-phenylpyrazol-3-yl][1,2,4]triazolo[4,3-a]quinoxalines 4a-c has been achieved upon treatment with aroylhydrazines in boiling butanol. Compounds 4a-c were smoothly acetylated by acetic anhydride to give their acetyl derivatives 5a-c in good yield. 4-[5-(Acetoxymethyl)-1-phenylpyrazol-3-yl]-1-methyl[1,2,4]triazolo[4,3-a]quinoxaline was prepared by ring closure of 2-hydrazino-3-[5-(hydroxymethyl)-1-phenylpyrazol-3-yl]quinoxaline 6 by the action of acetic anhydride. The reaction of 6 with acetylacetone afforded 3-[5-(hydroxymethyl)-1-phenylpyrazol-3-yl]-2-(3,5-dimethylpyrazol-1-yl)quinoxaline 8 . In addition, the reaction of 3 with sodium azide in boiling N, N-dimethylformamide yielded the fused tetrazolo[1,5-a]quinoxaline 9 . 相似文献
6.
Mesoionic imidazo[1,2-c]-pyrimidine-2,7-diones 1a-c , analogs of purine-2,8-dione, were prepared from 4-amino-l-methylpyrimidin-6-ones 6a-c . These mesoionic purinone analogs were found to exist predominantly in the C3-H tautomeric form 1 and to undergo hydrolytic ring-opening reactions to produce 2-(4-imidazol-idon-2-ylidenyl)acetamides. Reaction of 1c with dimethyl acetylene dicarboxylate produced triazacyclopent-[cd]indene 25 via 1,3-dipolar cycloaddition. 相似文献
7.
Kimiaki Imafuku Miyuki Sumio Hisashi Matsumura 《Journal of heterocyclic chemistry》1980,17(5):1057-1059
3-Methyl-1,8-dihydrocycloheptapyrazol-8-one hydrazone ( 5 ) reacted with triethyl ortho-formate, orthoacetate and orthopropionate to afford 2,2a,4,5-tetraazabenz[cd]azulene derivatives ( 7a-c ). 3-Methyl- ( 7b ) and 3-phenyl-substituted compounds ( 7d ) were also obtained by the reactions of 5 with acetyl and benzoyl chlorides, respectively. 相似文献
8.
The action of ammonium acetate on 5-arylidene-3-phenyl-2-methylmercaptohydantoins 1g,h in acetic acid led to the formation of the 5-arylidene-3-phenylhydantoin derivatives 4a,b . In absence of a solvent, ring opening and rearrangement took place with the formation of the 5-arylidene-N2-phenylglycocyamidine derivatives 7a-c . Compounds 7a-c reacted with methyl iodide to afford the corresponding 3-methyl derivatives 9a-c . The structures of the synthesised products were established and the mechanism proposed for the rearrangement reaction was discussed. 相似文献
9.
Taizo Hatta Shuntaro Mataka Masashi Tashiro Katsutoshi Numano Hiroshi Suzuki Akiyoshi Tori-I 《Journal of heterocyclic chemistry》1991,28(1):55-59
The effect of the [2.2.2]cyclophane ring structure on the reduction of 1,2,5-thiadiazole ring incorporated in cyclophanes 1a-c and 2a-c was investigated. When reduced by sodium metal in ethanol followed by acetylation, para[23]cyclophane 1 gave a mixture of the expected cis- and trans-diamides, 3 and 4 , in which 4 was the major product. On the other hand, reduction of 1 with lithium aluminum hydride proceeded in a cis-selective manner and gave 3 as a major product after a treatment of the reduced products with acetic anhydride. The reduction of metacyclophane 2 , which is less strained than 1 , proceeded exclusively in cis-fashion and a subsequent treatment of the reduction product with acetic anhydride gave only cis-diamide 6 . 相似文献
10.
Dong Han Kim Arthur A. Santilli Richard A. Fieber 《Journal of heterocyclic chemistry》1972,9(6):1347-1354
Syntheses of 11-acety1-2-phenylpyrimido[5,4-c][1,5]benzoxazepin-5(11H)one ( 16a ) and analogs ( 16b,c, 22 ) were described. The reaction of 4-chloro-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester ( 7 ) with 2-aminophenol afforded 4-(2-hydroxyanilino)-2-phenyl-5-pyrimidine-carboxylic acid ethyl ester ( 8a ). The latter was also prepared by catalytic reduction of 4-(2-nitrophenoxy)-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester ( 9 ), which was obtained from 7 and 2-nitrophenol. Involvement of 4-(2-aminophenoxy)-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester ( 12a ) in this reduction as an intermediate was demonstrated by an independent synthesis of 12a and its subsequent rearrangement to 8a. Hydrolysis of 8a or 12a gave 4-(2-hydroxyanilino)-2-phenyl-5-pyrimidinecarboxylic acid ( 15a ). Reaction of 15a with acetic anhydride afforded 16a , the first member of a novel ring system, the pyrimido[5,4- c ][1,5]-benzoxazepin. Additional examples ( 16b,c ) were prepared similarly. The corresponding 11-ethyl derivative ( 22 ) was prepared in similar fashion, starting with 7 and 2-ethylaminophenol. A possible reaction mechanism for the formation of 16a-c from 15a-c and acetic anhydride was discussed. 相似文献
11.
Mohamed Othman Pascal Pigeon Bernard Decroix 《Journal of heterocyclic chemistry》1998,35(6):1429-1433
A synthesis of the thieno[2′,3′(3′,2′ or 3′,4′):5,6]azocino[2,1-a]isoindole-7,13-diones 6a-c was developed from N-thienylethylphthalimides 3a-c using a Wittig reaction followed by a Friedel-Crafts cyclization of acetic acid derivatives 5a-c . Reduction of ketones 6a-c into alcohols 7a-c was stereo specific. 相似文献
12.
I. G. Davydenko Yu. L. Slominskii O. I. Kalchenko A. V. Gutov A. N. Chernega A. I. Tolmachev 《Russian Chemical Bulletin》2008,57(1):159-164
A procedure was developed for the synthesis of derivatives of the new heterocyclic system, benzo[cd]furo[2,3-f]indole, based on the cyclodehydration of 6-acylmethyloxy-1-alkyl-benzo[cd]indol-2(1H)-ones. Either 7- or 8-aryl derivatives of benzo[cd]furo[2,3-f]indol-4(5H)-ones can be prepared depending on the reaction conditions. The molecular and crystal structures of 7- and 8-phenylbenzo[cd]furo[2,3-f]indol-4(5H)-ones were established by X-ray diffraction. 相似文献
13.
Heterocyclic and Carbocyclic 12-π-and 14-π-Systems, 47th Commnunication1. Synthesis of 7,9-Dimethyl-4,5-dihydro-3H-benz[cd]azualene-3-one and 7,9-Dimethyl-3H-benz[cd]azulene-3-one. A Simple Synthesis of Azulenopseudophenalenons 4, 6, 8-Trimethylazulene ( 3 ) reacts after metalation with lithiumdiisopropyl-amide in ether with bromoacetic acid to the 6, 8-dimethylaltulene-4-propionic acid ( 4 ), which undergoes cyclization to the 7, 9-dimethyl-4, 5-dihydro-3H-benz [cd]-azulene-3-one ( 5 ) in the presence of p-toluenesulfonic acid; oxidation of 5 with 2, 3-dichloro-5, 6-dicyanobenzoquinone yields 7, 9-dimethyl-3H-benz [cd]azulene-3--one ( 1b ). Alkylation of 1b with triethyloxonium tetrafluoroborate in CH2C12 gives the 3-ethoxy [cd]benzazulenium tetrafluoroborate ( 6 ). 相似文献
14.
Vladimir L. Rusinov Grigori V. Zyryanov Tatjana L. Pilicheva Oleg N. Chupakhin Hans Neunhoeffer 《Journal of heterocyclic chemistry》1997,34(3):1013-1019
3-Aryl-1,2,4-triazin-5(2H)-ones 1a-c react with indoles 2a-c in trifluoroacetic acid/chloroform or in boiling butanol or acetic acid to give 3-aryl-6-(indolyl-3)-1,6-dihydro-1,2,4-triazin-5(2H)-ones 3a-g . Oxidation of the dihydro-1,2,4-triazin-5(2H)-ones 3a-e afforded 6-(indolyl-3)-1,2,4-triazin-5(2H)-ones 4a-e , products of nucleophilic substitution of hydrogen in 1a-c . Refluxing 1b with N-methylpyrrote 5b in butanol for an extended time resulted in the formation of 3-(4-chlorophenyl)-6-(1-meuiylpyrrolyl-2)-1,2,4-triazin-5(2H)-one 4h. The reaction of 1a-c with indoles 2a-c , pyrroles 5a,b , 1,3-dimethyl-2-phenylpyrazol-4-one (8) and aminothiazoles 9a,b in acetic anhydride affords the 1-acetyl-3-aryl-6-hetaryl-1,6-dihydro-1,2,4-triazin-5(2H)-ones 6a-s . Reaction of 1a-c with N-methyl-pyrrole 5b in acetic anhydride gives beside the 1:1 addition products 6h-k also the 2:1 addition products 7a-c . 相似文献
15.
Yoshihisa Kurasawa Yumiko Kamigaki Ho Sik Kim Rika Futatsukawa Megumi Kanoh Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1989,26(3):853-856
The pyrazolo[5′, 1′:3, 4][1, 2, 4]triazino[5, 6-d]pyrimidines 5a-c, 6 were synthesized from the pyrazolo[5, 1-c]-[1, 2, 4]triazines 1a, c and the ring carbon signals of 5a-c, 6 were assigned by the aid of coupling constant [J( 13 C-1H)] data. 相似文献
16.
A new series of 2,3-disubstituted quinoline derivatives were synthesized from 2-chloroquinoline-3-carbaldehyde. In the reaction sequence, acetanilide was cyclized to give 2-chloroquinoline-3-carbaldehyde 1 , which was transformed to 2-(4-phenylpiperazin-1-yl)quinolin-3-carbaldehyde 2 by reaction with 4-phenylpiperazine in DMF-containing anhydrous K2CO3; then, compound 2 was oxidized by iodine in methanol, and methyl 2-(4-phenylpiperazin-1-yl)quinoline-3-carboxylate 3 was synthesized. The key intermediate 4 , 4-amino-5-[2-(4-phenylpiperazin-1-yl)quinolin-3-yl]-4H-1,2,4-triazole-3-thiol, was prepared using the ester 3 by a series of step. Reaction of 5 with various aromatic carboxylic acids or phenacyl bromides yielded 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles 5a-c and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines 6a-c , respectively. Moreover, compound 2 condensed with o-phenylenediamine to give 2-[2-(4-phenylpiperazin-1-yl)quinolin-3-yl]-1H-benzimidazole 7 . Interaction of 7 and 2-chloromethyl-5-aryl-1,3,4-oxadiazoles in the presence of K2CO3 led to the title compounds 8a-c . Furthermore, 4,5-dihydroisoxazoline derivatives 9a-c were obtained by the reaction of readily accessible starting materials including 2-(4-phenylpiperazin-1-yl)quinolin-3-carbaldehyde 2 , 1-phenyl-2-(triphenylphosphoranylidene)ethanone and hydroximoyl chlorides under mild conditions in the presence of Et3N. The hydrazone intermediates 10a-c were obtained by the condensation of 2 with aroylhydrazides in ethanol, then, refluxing in acetic anhydride yielded 3-acetyl-5-aryl-2-[2-(4-phenylpiperazin-1-yl)quinolin-3-yl]-2,3-dihydro-1,3,4-oxadiazoles 11a-c . Structures of these compounds were established by their elemental analysis, IR, 1H NMR, and mass spectral data. 相似文献
17.
Hideo Kojima Kazuyoshi Ozaki Noboru Matsumura Hiroo Inoue 《Journal of heterocyclic chemistry》1990,27(6):1845-1846
7-Substituted 2,3-bis(isopropylthio)naphth[1,8-bc]azepines 3a-c were synthesized in good yields by the reactions of 5-substituted 1-naphthylamines 2a-c with tris(isopropylthio)cyclopropenylium perchlorate ( 1 ) in acetonitrile under reflux. This reaction proceeds through the facile ring opening of 1 , followed by the intermediary formation of iminium salts 5a-c and then intramolecular cyclization. 相似文献
18.
Dong Chan Kim Dong Jin Kim Sang Woo Park Kyung Ho Yoo 《Journal of heterocyclic chemistry》1995,32(5):1581-1586
The 1,4-dipolar cycloaddition of 3-phenyl-7-[N-pheny(carbamoyl)]-5,6-dihydroimidazo[2,1-b]thia-zolium betaine (7d) with a series of aliphatic alkylating agents such as ethyl bromoacetate, α-chloroacetone, and ethyl 4-chloroacetoacetate gave a variety of new ring-expanded cycloadducts 10a-c instead of ring transformation compounds 9 . This result was derived from the difference of reactivity between N- and S-alkylations of thiazolium betaines 7a,d. The advantage of our method is to prepare the triheterocyclic compounds 10a-c of complicated structure using reactive thiazolium betaine 7d in a one-pot without isolation of intermediates. Treatment of N-bridged thiazolo compounds 1a-c with benzoyl isothiocyanate led to new thiazolium betaines 2a-c , which were reacted with methyl iodide to afford the S-alkylated quarternary ammonium salts 3a-c. Synthesis of new 2-iminothiazolinium betaines 5a,b also was carried out. 相似文献
19.
Starting from 4-chlorocoumarin-3-carbaldehyde (1) and Wittig phosphoranes 2a-d the title compounds 6a-c have been synthesized via a four-step sequence. The intermediate 4-alkylamino-3-vinylcoumarins 5a-k have been prepared by the reaction of 4-chloro-3-vinylcoumarins 3a-d with primary amines 4a-h . The coumarin derivatives 5 (except 5k ) underwent an unusual pyridine ring closure under Vilsmeier conditions to form the benzopyrano[4,3-b]pyridines 6 . When the aminoaldehydes 7 were treated with the Wittig reagent 2b the fused N-alkyl-2 (1H) -pyridinones 8 have been obtained as expected. 相似文献
20.
H. D. Hollis Showalter Judith L. Johnson Jeanne M. Hoftiezer 《Journal of heterocyclic chemistry》1986,23(5):1491-1501
Synthetic methodologies to a number of 5- and 7-chloroanthra[1,9-cd|pyrazol-6(2H)-ones, 4 and 37 respectively, optionally substituted with side chains at N-2 and dioxy substituents in the A ring, are reported. Reported also are detailed uv, ir and 1H-nmr spectroscopy for representative compounds. 相似文献