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1.
Yoshihisa Kurasawa Megumi Kanoh Yumiko Kamigaki Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(3):1015-1018
The reactions of the pyrazole-5-diazonium salt 3 with malononitrile and ethyl cyanoacetate gave 4-amino-3-cyano-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazine 7 and 4-amino-3,8-bisethoxycarbonylpyrazolo[5,1-c]-[1,2,4]triazine 8 , whose reactions with p-chloroaniline hydrochloride afforded 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)amidinopyrazolo[5,1-c][1,2,4]triazine 9 and 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)car-bamoylpyrazolo[5,1-c][1,2,4]triazine 10 , respectively. The reactions of 7 and 8 with o-phenylenediamine di-hydrochloride provided 9-ethoxycarbonyl-13H-spiro[benzimidazole-2′(3′H),6(5H)-pyrazolo[1,5′:3,4][1,2,4]tri-azino[5,6-b][1,5]benzodiazepine] hydrochloride 11a and 9-ethoxycarbonyl-6-oxo-13H-5,6-dihydropyrazolo-[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepine 12 , respectively. The antifungal activity of the above compounds was described. 相似文献
2.
Issa Yavari Zinatossadat Hossaini Maryam Sabbaghan Majid Ghazanfarpour-Darjani 《Monatshefte für Chemie / Chemical Monthly》2007,138(7):677-681
Summary. The 1,3-dipolar intermediates generated by addition of isoquinoline, to dialkyl acetylenedicaboxylates are trapped by N-alkylisatins to produce dialkyl 1,2-dihydro-2-oxo-1-alkylspiro[3H-indol-3,2′-[2H,11bH][1,3]oxazino[2,3-a]isoquinoline]-3′,4′-dicarboxylates in excellent yields. The reaction of isoquinoline, quinoline, or pyridine with dimethyl
acetylenedicarboxylate in the presence of ninhydrin led to dimethyl 1,2-dihydro-1,3-dioxospiro[3H-indene-3,2′-[2H,11bH][1,3]oxazino[2,3-a]isoquinoline]-3′,4′-dicarboxylate, dimethyl 1,2-dihydro-1,3-dioxospiro[3H-indene-3,3′[3H,4aH][1,3]oxazino[3,2-a]quinoline]-1,2-dicarboxylate, or dimethyl 1,2-dihydro-1,3-dioxospiro[3H-indene-3,2′-[2H,9aH]pyrido[2,1-b][1,3]oxazino]-3,4-dicarboxylate. 相似文献
3.
Yoshinori Tominaga Raymond N. Castle N. Kent Dalley 《Journal of heterocyclic chemistry》1993,30(1):295-299
The Diels-Alder reaction of 5-amino-1-(p-toluenesulfonyl)pyrazole-4-carbonitrile with dimethyl acetylenedi-carboxylate was carried out in the presence of potassium carbonate in dimethyl sulfoxide. The reaction gave dimethyl 2-(p-toluenesulfonylamino)-3-cyano-4-imino-1,4-dihydropyridine-5,6-dicarboxylate. The product was formed by transformation of the original Diels-Alder adduct followed by rearrangement of the p-toluenesul-fonylamino group into the 2-position of the pyridine ring. The structure of the product was irrefutably established by X-ray crystallography. This reaction is the first example of a pyrazole ring serving as the diene in a [4 + 2] cycloaddition reaction. 相似文献
4.
Yoshihisa Kurasawa Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(6):1799-1801
Novel 3-substituted 4-amino-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazines 7,8 were synthesized by the reactions of malononitrile and ethyl cyanoacetate with the pyrazole-5-diazonium salt 3 . Moreover, compounds 7,8 were converted into the pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepines 9, 10 . 相似文献
5.
Shunsaku Shiotani Youichi Tsukamoto Yasuyuki Kitagawa 《Journal of heterocyclic chemistry》1997,34(1):129-141
Furo[3,2-c]-( 1a ), -[2,3-c]- ( 1b ) and -[3,2-b]pyridine ( 1c ) were reacted with isopropyl chloroformate and trimethyl phosphite to give dimethyl 5-isopropoxycarbonyl-4,5-dihydrofuro[3,2-c]pyridine-4-phosphonate ( 2a ), dimethyl 6-isopropoxycarbonyl-6,7-dihydrofuro[2,3-c]pyridine-7-phosphonate ( 2b ) and dimethyl 4-isopropoxycarbonyl-4,7-dihydrofuro[3,2-b]pyridine-7-phosphonate ( 2c ) as unstable syrups. Reaction of 2b and 2c with n-butyllithium and then with benzaldehyde, p-methoxybenzaldehyde, p-cyanobenzalde-hyde or propionaldehyde afforded the normal Wittig reaction products 5b-H, 5b-OMe, 5b-CN, 5b-Et, 5c-H, 5c-H, 5c-OMe and 5c-CN , except for 2b with propionaldehyde. While, the same reactions of compound 2a and the reaction of 2b with propionaldehyde afforded the unexpected products, 5-isopropoxycar-bonylfuro[3,2-c]pyridinio-4-aryl-(or ethyl)methoxides 3a-H, 3a-OMe, 3a-CN and 3a-Et , 4-(1′-aryl(or ethyl)-1′-hydroxymethyl)furo[3,2-c]pyridines 4a-H, 4a-OMe, 4a-CN and 4a-Et accompanying formation of the normal products. Treatment of the normal Wittig reaction products with lithium diisopropylamide and then with acetone gave the derivatives alkylated at the 2-or the benzylic positions. 相似文献
6.
Mohamed Hilmy Elnagdi Mohamed Riffat Hamza Elmoghayar Ezzat Mohamed Kandeel Mohamed Kamal Ahmed Ibrahim 《Journal of heterocyclic chemistry》1977,14(2):227-230
3-Phenylpyrazole-5-(liazonium chloride ( 1 ) couples with α-chloro derivatives of acetylacetone, ethyl acetoacetate and aceto-o-anisidine to yield the corresponding pyrazole-5-yl hydrazonyl chloride derivatives 2a-c . Compounds 2a,b were cyclised to yield either the pyrazolo[1,5-c]-1,2,4-triazole derivatives 3a,b or the pyrazolo[1,5-c]-as-triazines 4a,b depending on the applied reaction conditions. Compound 2c cyclised only into 3c under different cyclization conditions. The pyrazolo[1,5-c]-as-triazine derivatives 4c-e could be prepared via condensation of 2a with potassium cyanide. Compound 2d reacted with aromatic thioles and with sodium benzene-sulphonate to yield the pyrazolo[1,5-c]-as-triazine derivatives 6a-d . Compound 1 reacted with activated double bond systems to yield pyrazolo[1,5-c]-as-triazines 8a,b and 9 . 相似文献
7.
Yoshihisa Kurasawa Ritsuko Katoh Tomomi Kureyama Noriko Yoshishiba Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1992,29(6):1649-1651
The reaction of 6-chloro-2-[2-(p-chlorobenzylidene)-1-methylhydrazino]quinoxaline 4-oxide 3a or 2-[2-(p-bromobenzylidene)-1-methylhydrazino]-6-chloroquinoxaline 4-oxide 3b with dimethyl acetylenedicarboxylate under reflux in N,N-dimethylformamide resulted in deoxygenation to give 6-chloro-2-[2-(p-chlorobenzylidene)-1-methylhydrazino]quinoxaline 4a or 2-[2-(p-bromobenzilidene)-1-methylhydrazino]-6-chloroquinoxaline 4b , respectively, while the reaction of compound 3a or 3b with dimethyl acetylenedicarboxylate under reflux in dioxane precipitated dimethyl 8-chloro-4-[2-(p-chlorobenzyli-dene)-1-methylhydrazino]-3aH-isoxazolo[2,3-a]quinoxaline-2,3-dicarboxylate 6a or dimethyl 4-[2-(p-bromobenzylidene)-1-methylhydrazino]-8-chloro-3aH-isoxazolo[2,3-a]quinoxaline-2,3-dicarboxylate 6b , respectively. Further refluxing of compound 6a or 6b in N,N-dimethylformamide provided compound 4a or 4b , respectively. 相似文献
8.
Giorgio Stefancich Marino Artico Romano Silvestri 《Journal of heterocyclic chemistry》1992,29(2):487-491
The synthesis of 8H-diimidazo[1,5-a:2′,1′-c][1,4]benzodiazepine 6 , a novel nitrogen-containing tetracyclic ring, is reported starting from 5H-imidazo[2,1-c][1,4]benzodiazepine 7. Reaction of this compound with nitromethane and subsequent reduction of the obtained nitromethyl derivative 8 afforded 11-aminomethyl-10,11-dihydro-5H-imidazo[2,1-c][1,4]benzodiazepine 9. Treatment of the latter compound with formaldehyde led to 1,2,3,3a-tetrahydro-8H-diimidazo[1,5-a:2′,1′-c][1,4]benzodiazepine 10 , which was then oxidized to the title compound. 相似文献
9.
Giorgio Stefancich Romano Silvestri Marino Artico 《Journal of heterocyclic chemistry》1993,30(2):529-532
Reaction of 2-nitrobenzyl iodide with 1H-imidazole, in the presence of potassium tert-butoxide and 18-crown-6, gave 1-(2-nitrobenzyl)-1H-imidazole. Trichloroacetylation of this compound furnished trichloroacet-ylimidazole 8 , which on treatment with sodium ethoxide was transformed into the corresponding ethoxycarbonyl derivative 9 . Catalytic reduction of the nitro group to the amino group yielded 10 , which was then cyclized to 10,11-dihydro-11-oxo-5H-imidazo[2,1-c][1,4]benzodiazepine 11. Treatment of this lactam with di-4-morpholinylphosphinic chloride followed by reaction of the intermediate 12 with formylhydrazine gave the title compound or its 1-derivatives when acetylhydrazine or isonicotinoylhydrazine were used instead of formylhydrazine. 相似文献
10.
Versatile 2-thioxopyrimidine-type building blocks ethyl 3-(2-ethoxy-2-oxoethyl)- 4 -oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7-carboxylate ( 4 ) and ethyl 4-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7-carboxylate ( 8 ) were synthesized from diethyl 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3,6-dicarboxylate ( 1 ). Derivatives of linear and angular heterocyclic systems having the imidazole and 1,2,4-triazole ring were obtained from the key intermediates 4 and 8 , respectively. 相似文献
11.
Sanaa O. Abd Allah Hamdy A. Hammouda Fatma A. Ali 《Journal of heterocyclic chemistry》1985,22(2):497-500
5-Salicylidenethiazolidine-2,4-dithione ( 1 ) reacts with acrylonitrile, N-phenylmaleimide and dimethyl acet-ylenedicarboxylate to afford the fused thiopyrano[2,3-d]thiazolidinethione derivatives 2, 4 and 6 , respectively. The salicylidene derivative 1 reacts with ethyl acrylate and malononitrile to afford the fused [1]benzopyrano[3′,4′:4,5]thiopyrano[2,3-d]thiazoles 3 and 9 , respectively. 4-Phenylhydrazono-2-thiazolidinethione ( 11 ) reacts with ethyl bromoacetate and/or phenacyl bromide to yield the fused thiazolo[3,4-c]triazines 13 and 14. 相似文献
12.
We have synthesized 5H-imidazo[2,1-c]pyrrolo[1,2-a][1,4]benzodiazepine 1 in five steps from 1-(2-amino-methylphenyl) pyrrole 4 . Amidino derivatives 11-12 have also been prepared. 相似文献
13.
An efficient one-pot synthesis of 6-amino-4-(2-chloroquinolin-3-yl)-3-methyl-2, 4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile derivatives (4a–f)(5a–f) by three component reactions of 2-chloroquinolin-3-carbaldehyde derivatives, malanonitrile, and 3-methyl pyrazolin-5-one derivatives catalyzed by L-proline in ethanol medium under mild conditions is established. The synthesized compounds were evaluated for antimalarial activity and the LC50/LC90 values were described. Compounds 4d, 5d, and 5f exhibits good antimalarial activity when compared to other pyrano[2,3-c]pyrazole scaffolds. 相似文献
14.
Stanfield Y. Lee Jinwon Seo Christopher W. Bielawski 《Journal of polymer science. Part A, Polymer chemistry》2020,58(12):1687-1698
Two diastereomeric derivatives of norbornene, dimethyl (1R,2R,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate and dimethyl (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate, were synthesized and polymerized using ring-opening metathesis polymerization (ROMP). For comparative purposes, diastereomeric derivatives of Dewar benzene, dimethyl (1R,2S,3R,4S)-bicyclo[2.2.0]hex-5-ene-2,3-dicarboxylate and dimethyl (1R,2S,3S,4S)-bicyclo[2.2.0]hex-5-ene-2,3-dicarboxylate, were also synthesized and polymerized using ROMP. The polymerization reactions proceeded in a controlled manner as evidenced in part by linear relationships between the monomer-to-catalyst feed ratios and the molecular weights of the polymer products. Chain extension experiments were also conducted which facilitated the formation of block copolymers. Although the poly(norbornene) derivatives exhibited glass transition temperatures that were dependent on their monomer stereochemistry (cis: 115°C vs. trans: 125°C), more pronounced differences were observed upon analysis of the polymers derived from Dewar benzene (cis: 70°C vs. trans: 95°C). Likewise, microphase separation was observed in block copolymers that were prepared using the diastereomeric monomers derived from Dewar benzene but not in block copolymers of the norbornene-based diastereomers. The differential thermal properties were attributed to the relative monomer sizes as reducing the distances between the polymer backbones and the pendant stereocenters appeared to enhance the thermal effects. 相似文献
15.
Giorgio Stefancich Marino Artico Romano Silvestri 《Journal of heterocyclic chemistry》1992,29(4):1005-1007
Reaction of di-4-morpholinylphosphinic chloride on 5,10-dihydro-9H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one 9 afforded 11-(di-4-morpholinylphosphinyloxy)-5H-pyrrolo[2,1-c][1,4]benzodiazepine 10 . Displacement of di-4-morpholinylphosphinyloxy group of 10 by formylhydrazine with concomitant intramolecular cyclization led directly to 9H-pyrrolo[2,1-c]-s-triazolo[4,3-a][1,4]benzodiazepine 7, a novel nitrogen heterocyclic ring of pharmaceutical interest. A new procedure for the synthesis of 9 is also described. 相似文献
16.
Litvinov Yu. M. Rodinovskaya L. A. Shestopalov A. M. 《Russian Chemical Bulletin》2009,58(11):2362-2368
A new convenient method for the synthesis of 6-amino-2H,4H-pyrano[2,3-c]pyrazole-5-carbonitriles, namely, four-component condensation of carbonyl compounds (aromatic aldehydes, heterocyclic ketones),
malononitrile, β-keto esters, and hydrazine hydrate in ethanol in the presence of triethylamine as a catalyst, which occurs
selectively, is developed. One-pot two-step modification of this method is proposed for the synthesis of spiro[(3 H)-indole-3,4 ′-(4′H)-pyrano[2,3-c]pyrazol]-2-ones. 相似文献
17.
Norman W. Gilman Betty C. Holland R. Ian Fryer 《Journal of heterocyclic chemistry》1977,14(7):1163-1169
The syntheses of novel 8-chloropyrazolo[1,5-a][1,4]benzodiazepines and of an imidazo-benzodiazepinone utilizing products from the nucleophilic substitution of fluorine in 2-fluoro-5-nitrobenzophenone ( 1 ) by pyrazole-3,5-dicarboxylic acid, dimethyl ester ( 2 ) and by 2-methyl-imidazole-4,5-dicarboxylic acid, diethyl ester ( 30 ) are described. 相似文献
18.
1,3,4,6,8-Pentamethylazulene ( 9 ), when heated at 100° in supercritical CO2 at 150 bar in the presence of 4 equiv. of dimethyl acetylenedicarboxylate (ADM), led to the formation of 16% of a 1:1 mixture of dimethyl 3,5,6,8,10-pentamethylheptalene-1,2-dicarboxylate 12a ) and its double-bond-shifted isomer 12b as well as 4% of the corresponding azulene-1,2-dicarboxylate 13 (Scheme 4). The formation of the [1 + 2] adduct 11 (cf. Scheme 2) was not observed. Similarly, benz[a]azulene ( 25 ) yielded in supercritical CO2 (150°/170 bar) in the presence of 4 equiv. of ADM dimethyl benzo[d]heptalene-6,7-dicarboxylate ( 29 ; 30%) and dimethyl benzo[a]cyclopent[cd]azulene-1,2-dicarboxylate ( 28 ; 22%; Scheme 5). The reaction of 5,9-diphenylbenz[a]azulene ( 26 ) and ADM in supercritical CO2 (100°/150 bar) gave the corresponding benzo[d]heptalene-6,7-dicarboxylate 31 (22%) and dimethyl 5,9-diphenyl-4b,10-etheno-10H-benz[a]azulene-11,12-dicarboxylate( 30 ; 25%; Scheme 5). 相似文献
19.
Maria Rosaria Del Giudice Anna Borioni Carlo Mustazza Franco Gatta 《Journal of heterocyclic chemistry》1994,31(6):1503-1507
A number of 2-aryl-substituted pyrido[3,2-e] and [4,3-e][1,2,4]triazolo[1,5-c]pyrimidines and [1,2,4]triazolo[1,5-c]pteridines 11,12a,b,e , their corresponding 5-carbonyl derivatives 7,8a,b,e and some pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ones 7,8c,d have been synthesized, according to different pathways. The new tricyclic heterocycles were prepared with the aim of studying their possible benzodiazepine receptors affinity. 相似文献
20.
By the action of thionyl chloride on 3(5)-R-4-phenacylpyrazole-5(3)-carboxylic acid ( 3c,d ), 3-R-5-phenylpyrano[3,4-c]pyrazole-7-(1H)ones ( 4c,d ) were obtained. When 4c,d were treated with hydrazine hydrate followed by refluxing in ethanol containing acetic acid, 4,7-dihydro-3-R-5-phenylpyrazolo[3,4-d][1,2]-diazepin-8-(1H)ones ( 6c,d ) were formed. Compounds 6c,d , in turn, were refluxed in ethanol saturated with hydrochloric acid to yield 6-amino-1,6-dihydro-3-R-5-phenyl-7H-pyrazolo[3,4-c]pyridin-7-ones ( 7c,d ). Compounds 7c,d could be obtained directly from 5c,d. The starting materials 3c,d were prepared by hydrolysis of the oxime of 3(5)-R-4-phenacyl-5(3)carboalcoxypyrazoles ( 1a,b ). Structural assignments rested on correct elemental analysis, molecular weights determined by mass spectrometry, and spectroscopic evidence. 相似文献