共查询到20条相似文献,搜索用时 31 毫秒
1.
Roman A. Irgashev Nadezhda S. Demina Nikita A. Kazin Gennady L. Rusinov 《Tetrahedron letters》2019,60(16):1135-1138
Two new classes of heteroacenes, namely benzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]quinolines and benzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2-b][1,8]naphthyridines, have been formed using the Friedländer reaction to annulate the benzo[b]thieno[2,3-d]thiophene scaffold to quinoline or 1,8-naphthyridine fragments. In accordance with this synthetic strategy, benzo[b]thieno[2,3-d]thiophen-3(2H)-ones were treated with 2-aminobenzaldehydes or 2-aminonicotinaldehyde in the presence of pyrrolidine in glacial acetic acid at reflux to give the desired quinoline- or 1,8-naphthyridine-fused compounds, respectively. The optical and electrochemical properties of selected heteroacenes were determined. 相似文献
2.
Masahiko SaitoItaru Osaka Eigo MiyazakiKazuo Takimiya Hirokazu KuwabaraMasaaki Ikeda 《Tetrahedron letters》2011,52(2):285-288
Simple one-step synthesis of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) from commercially available o-chlorobenzaldehyde is reported. The procedure is also applicable to the synthesis of dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DNTT). 相似文献
3.
Gas-phase thermolysis of thieno[3,2-e][1,2,4]triazines gave benzonitrile, isothiazole, pyrimidine, [1]benzothieno[2,3-d]pyrimidine and thieno[3,2-d]thiazole derivatives. A mechanism of these pyrolytic transformation was proposed. Two new and efficient syntheses of the starting thieno[3,2-e][1,2,4]triazines were reported. 相似文献
4.
Synthesis,Reactions, and Antimicrobial Evaluation of Some Polycondensed Thienopyrimidine Derivatives
Some novel indeno[2,1-b]thiophenes, indeno[1′,2′:4,5]thieno[2,3-d][1,2,3]triazines, indeno[1′,2′:4,5]thieno[2,3-d]pyrimidines, indeno[1′,2′:4,5]thieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidines, and indeno[1′,2′:4,5]thieno[2,3-d][1,2,4]triazolo[4,3-a]pyrimidines 2–16 were prepared starting with 2-aminoindeno[2,1-b]thiophene-3-carboxylic acid amide ( 1 ). Furthermore, the antimicrobial evaluation of the prepared products showed that many of them revealed promising antimicrobial activity. 相似文献
5.
L. Yu. Chumakova A. M. Demchenko A. N. Krasovsky T. V. Dolishnyak M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2003,39(8):1002-1012
3-Ethoxycarbonyl-2-(N-R-thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophenes were obtained by the reaction of 2-amino-3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene with isothiocyanates and of 3-ethoxycarbonyl-2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]thiophene with primary and secondary amines. The cyclization paths of the products leading to derivatives of thieno[2,3-d]pyrimidine and thieno[2,3-d]-1,3-thiazine were studied. The corresponding S-substituted derivatives were obtained by the alkylation of 3-R-2-thioxo-3,4,5,6,7,8-hexahydrobenzo[b]thieno[2,3-d]pyrimidin-4-ones. 相似文献
6.
The thieno[3,2-e][1,4]diazepin-2-one ( 1a ), the thieno[2,3-e] [ 1,4] diazepin-2-one ( 1b ), the pyrazolo[3,4-e][1,4]diazepin-2-one ( 1c ) and a chloro analog of 1b , compound 1d , were each converted to derivatives of the novel tricyclic ring systems 4H-imidazo[1,5-a]thieno[2,3-f] [1,4]-diazepine, 4Himidazo[1,5a]thieno[2,3f][1,4]diazepine and 4H-imidazo[ 1,5-a]pyrazolo[4,3-f]-[1,4]diazepine. Depending on the substituents desired on the imidazo ring, two different synthetic pathways were employed. 相似文献
7.
Yuta Ogawa Erika Takiguchi Masashi Mamada Daisuke Kumaki Shizuo Tokito Hiroshi Katagiri 《Tetrahedron letters》2017,58(10):963-967
Two novel bent-shaped thienoacenes, naphtho[2,3-b]naphtho[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DNTT) and anthra[2,3-b]anthra[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DATT) were synthesized from thieno[2,3-b]thiophene and their corresponding aromatic anhydrides by three steps: Friedel–Crafts acylation, acid-promoted cyclization, and reductive aromatization. The structural curvature improved the solubility of these thienoacenes in organic solvents. The bent-DNTT based FET device was fabricated by the spin-coating method. The device exhibited p-type characteristics with a mobility of 5.1 × 10?5 cm2 V?1 s?1. Its thin-film structure was fully characterized as an edge-on orientation with large intermolecular orbital coupling. 相似文献
8.
The syntheses of two novel pentacyclic ring systems, the thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepino-[4,5-a]benzimidazole and the indazolo[2,3-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine are described. Attachment of a propargyl linked quinolinone resulted in compounds 6 and 16 which showed PAF-antagonist activity by the intravenous route of administration in guinea pigs. The more potent compound 16 also exhibited good oral activity with an ID50 of 0.2 mg/kg in the bronchoconstriction assay. 相似文献
9.
A novel I2-catalyzed one-pot multicomponent protocol for the synthesis of a variety of elusive furo[2,3-b]pyrrole and thieno[2,3-b]pyrrole libraries has been established. To date, cyclization among alkanone, hydrazine and 2-bromobenzofuran or 2-bromobenzo[b]thiophene has not been explored in one-pot. Thus, the proposed single step protocol provides a versatile alternative to existing routes for accessing useful furo[2,3-b]pyrrole and thieno[2,3-b]pyrrole libraries. 相似文献
10.
A. I. Vas’kevich R. I. Vas’kevich V. I. Staninets S. A. But A. N. Chernega 《Russian Journal of Organic Chemistry》2007,43(10):1526-1531
2-(2-propynylsulfanyl)-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-one with arylsulfenyl chlorides in chloroform gave products of anti-Markownikoff Ad E-addition. The use of nitromethane as solvent in the presence of lithium perchlorate additives favored intramolecular electrophilic cyclization into 1-arylsulfanyl-1,2,6,7,8,9-hexahydro-4H-benzo[4,5]thieno[3,2-e][1,3]thiazolo[3,2-a]-pyrimidin-5-one. 相似文献
11.
S. M. Khripak Mikhail V. Slivka Marina V. Slivka V. G. Lendel 《Russian Journal of Organic Chemistry》2007,43(3):439-442
Reactions of [1]benzothieno[3,2-e][1,3]oxazolo[3,2-a]pyrimidin-11-ium bromide with oxygen-containing nucleophiles involve opening of the dihydrooxazole ring and lead to the formation of new functionally substituted thieno[2,3]-d]pyrimidine derivatives. 相似文献
12.
Sobhi M. Gomha 《Monatshefte für Chemie / Chemical Monthly》2009,32(7):213-220
Abstract
The reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride to afford the non-isolable azo-coupling products which converted, in situ, to 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some of the newly synthesized compounds had a moderate effect against some bacterial and fungal species. 相似文献13.
4,8-Dimethyl-6,7,8,9-tetrahydropyrido[4′,3′:4,5]thieno[2,3-e][1,2,4]triazolo[3,4-a]-4H-pyrimidin-5-ones, 7-methyl-2,3,6,7,8,9-hexahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrrolo[1,2-a]-1H, 10H-pyrimidin-10-one, 8-methyl-1,2,3,4,7,8,9,10-octahydropyrido[4′,3′:4,5]thieno[2,3-d]-11H-pyrimidin-11-one, and 9-methyl-2,3,4,5,8,9,10,11-octahydro[4′,3′:4,5]thieno[2,3-d]azepino-[1,2-a]-1H, 12H-pyrimidin-12-one which consist four new heterocyclic ring systems were synthesized from 2-amino-3-carbethoxy-5-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine. 相似文献
14.
Helmut Link 《Helvetica chimica acta》1990,73(4):797-803
Synthesis of 2,4-Diamino-thieno[2,3-d]pyrimidines Condensation of 2-aminothiophene-3-carbonitrile ( 4 ) with guanidine or sequential addition of CS2 and NH3 to 4 provides 2,4-diaminothieno[2,3-d]pyrimidine ( 7 ). This compound yields, after sequential addition of sec-BuLi and either [3-(trifluoromethyl)benzene]sulfenyl chloride ( 8 ) or the corresponding disulfide 9 , followed by acidic work up, 2,4-diamino-6-{[3-(trifluoromethyl)phenyl]thio}thieno[2,3-d]pyrimidine ( 10 ). In another approach, 2-amino-5-{[3-(trifluoromethyl)phenyl]thio}thiophene-3-carbonitrile ( 11 ) obtained from 4 and 8 is transformed to 10 by condensation with guanidine. Corresponding to the second route, 2,4-diamino-6-[(naphth-2-yl)thio]thieno-[2,3-d]pyrimidine ( 16 ) is synthesized. Oxidation of 10 with m-chloroperbenzoic acid gives 2,4-diamino-6-{[3-(tri-fluoromethyl)phenyl]sulfinyl}thieno[2,3-d]pyrimidine ( 13 ). 相似文献
15.
Mono(iminophosphorane) 4 was selectively prepared from the reaction of 3,4-diaminothieno[2,3-b]thiophene 3 with excess triphenylphosphine, C2Cl6, and Et3N due to intramolecular double hydrogen bond formation. Mono(iminophosphorane) 4 reacted with aromatic isocyanates to give stable carbodiimides 8, which were further treated with aliphatic secondary or primary amines to give 2-amino substituted thieno[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones 10 or 12 in the presence of a catalytic amounts of EtO−Na+. However, in the presence of a catalytic amounts of potassium carbonate, the carbodiimides 8 were transformed into previously unreported 5H-2,3-dithia-5,7-diaza-cyclopenta[c,d]indenes 13 via direct cyclization in high yields. The reaction of carbodiimides 8 with phenols in the presence of a catalytic amounts of potassium carbonate gave a mixture of 2-aryloxy substituted thieno[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones 14 and 13. X-ray structure analysis of 10m supported the structure and the proposed reactivity of amino group. 相似文献
16.
Sobhi M. Gomha 《Monatshefte für Chemie / Chemical Monthly》2009,140(2):213-220
Abstract The reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride
to afford the non-isolable azo-coupling products which converted, in situ, to 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some
of the newly synthesized compounds had a moderate effect against some bacterial and fungal species.
Graphical abstract
相似文献
17.
The synthesis and selected reactions of 2-amino-3-(cyanomethylsulfonyl)thiophene is reported. In particular, cyclization reaction of the versatile aminothiophene yielded a number of novel thieno[3,2-b][1,4]-thiazine 1,1-dioxides, as well as the analogous thieno[2,3-e][1,3,4]thiadiazine 4,4-dioxide. Reaction of the thienothiazine system with hydrazine was subsequently explored, which resulted in either ring-opening of the thiazine and formation of an aminopyrazole or solely ring cleavage depending on the thiazine substituent. Additionally, the synthesis of bis(2-amino-3-thienyl)sulfone and the corresponding bis-acetamide is described. 相似文献
18.
Nazariy T. Pokhodylo Olga Ya. Shyyka Roman D. Savka Mykola D. Obushak 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2092-2100
Novel transformations of the amino and carbonyl/nitrile groups in the Gewald thiophenes were studied for thienopyrimidine synthesis. It was found that 2-amino-thiophene-3-carboxamides and ethyl 2-(acetylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carbo- xylate did not yield tetrazole derivatives, neither in the reaction with triethyl orthoformate and sodium azide, nor in the reaction with phosphorus oxychloride and sodium azide, correspondingly. On the contrary, derivatives of thieno[2,3-d]pyrimidin-4(3H)-one and thieno[2,3-d][1,3]oxazin-4-one were isolated. New 2-azidothiophenes [2-azido-4,5,6,7-tetra hydro-1-benzothiophene-3-carbonitrile and 2-azido-4,5,6,7-tetrahydro-1-benzothiophen-3-yl(phenyl)methanone] were synthesized and used in anionic domino reactions with activated acetonitriles to yield thieno[3,2-e][1,2,3]triazolo[1,5-a]pyrimidines and/or 2-(5-amino-1H-1,2,3-triazol-1-yl)thiophenes. Finally, a new ring system of thieno[3,2-e]pyrazolo[1,5-a]pyrimidine was synthesized via a domino reaction of ethyl 2-[(2Z)-2-(1-chloro-2-ethoxy-2-oxoethylidene)hydrazino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate with activated acetonitriles. 相似文献
19.
Raymond N. Castle Sudabeh Pakray Gary E. Martin 《Journal of heterocyclic chemistry》1991,28(8):1997-2003
Five novel polycyclic heterocyclic ring systems are reported via photocyclization. The specific final products in these ring systems are: naphtho[1′,2′:4,5]thieno[2,3-c][1,8]naphthyridin-6(5H)-one ( 5 ), naphtho-[1′,2′:4,5]thieno[2,3-c][1,6]naphthyridin-6(5H)-one ( 6 ), naphtho[1′,2′:4,5]thieno[2,3-c]-1,5-naphthyridine ( 9 ), naphtho[1′,2′:4,5]thieno[2,3-c][1,2,4]triazolo[4,3-a]-1,5-naphthyridine ( 12 ), and naphtho[2′,1′:4,5]thieno[2,3-c]-1,5-naphthyridine ( 17 ). The direction of photocyclization to produce 9 was established from a zero quantum two-dimensional nmr spectroscopy experiment (ZQCOSY) using 6-chloronaphtho[1′,2′:4,5]thieno[2,3-c]-1,5-naphthyridine ( 8 ) as the model compound. 相似文献
20.
Kerry M. ORourke Erin S. Johnstone Holger M. Becker Sally L. Pimlott Andrew Sutherland 《Tetrahedron》2018,74(30):4086-4094
The thieno[2,3-d]pyrimidinedione core is found as a component in a range of pharmaceutically active compounds, however, synthetic approaches to these scaffolds rely on access to functionalised, highly substituted thiophenes. Here we describe a new approach for the preparation of 5-carboxamide-6-aryl analogues that involves a two-step synthesis of the thieno[2,3-d]pyrimidinedione core from a readily available mercaptouracil derivative. Thio-alkylation with ethyl 3-bromopyruvate, followed by cyclisation and dehydration mediated by polyphosphoric acid allowed the scalable synthesis of the thieno[2,3-d]pyrimidinedione unit. The late-stage functionalisation of this core motif via bromination of the thiophene ring and a subsequent Suzuki-Miyaura reaction as the key steps permitted access to a novel library of 5-carboxamide-6-aryl analogues. The physicochemical properties of these compounds were determined, generating an insight into the potential bioavailability of these scaffolds. Based on these results, a selection of the novel 5-carboxamide-6-aryl analogues were tested as lactate uptake inhibitors of monocarboxylate transporters 1, 2 and 4 in Xenopus oocytes. 相似文献