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1.
The reaction of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate ( 1 ) with methanesulfonamide gave methyl 2-[(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridine-carboxylate ( 2 ). Alkylation of compound 2 with methyl iodide followed by cyclization of the resulting methyl 2-[methyl(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridinecarboxylate ( 3 ) yielded 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 4 ). The reaction of compound 4 with α,2,4-trichlorotoluene, methyl bromopropionate, methyl iodide, 3-trifluoromethylphenyl isocyanate, phenyl isocyanate and 2,4-dichloro-5-(2-propynyloxy)phenyl isothiocyanate gave, respectively, 4-[(2,4-dichlorophenyl)methoxy]-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazine 2,2-dioxide ( 5 ), methyl 2-[[1-methyl-2,2-dioxido-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4-yl]oxy]propanoate ( 6 ), 1,3,3-trimethyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 7 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-[3-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 8 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-phenyl-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 9 ) and N-[2,4-dichloro-5-(2-propynyloxy)phenyl]-4-hydroxy-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2] thiazine-3-carboxamide 2,2-dioxide ( 10 ). 相似文献
2.
Charles Y. Fiakpui Oludotun A. Phillips K. S. Keshava Murthy Edward E. Knaus 《Journal of heterocyclic chemistry》1999,36(2):377-380
A group of 5-(2-chlorophenyl)-10-(substituted)-7H-pyrido[4,3-f][1,2,4]triazolo[4,3-a][1,4]diazepines 7a-c were synthesized by the acid catalyzed reaction of 5-(2-chlorophenyl)-2-hydrazino-3H-pyrido[3,4-e]-[1,4]diazepine ( 6 ) with either trimethyl orthoformate, triethyl orthoacetate or triethyl orthobenzoate, respectively. 5-(2-Chlorophenyl)-7H-pyrido[4,3-f][1,2,4]triazolo[4,3-a][1,4]diazepine ( 7a ) and 5-(2-chlo-rophenyl)-10-methyl-7H-pyrido[4,3-f][1,2,4]triazolo[4,3-a][1,4]diazepine ( 7b ) exhibited good anticonvulsant activity in the subcutaneous metrazol anticonvulsant screen which serves as a model for absence (petit mal) epilepsy. 相似文献
3.
The condensation of 4-amino-2,1,3-benzothiadiazole (IV) with diphenyliodonium-2-earboxylate gave N-(2,1,3-benzothiadiazoI-4-yl)anthranilic acid (V) (28%), which was cyclized with phosphorus oxychloride to 6-chloro[1,2,5]thiadiazolo[3,4-c]acridine (VI) (84%). Treatment of VI with 3-(dimethylamino)-1-propanethiol hydrochloride in phenol afforded 6-[ [3-(dimethylamino)-propyl]thio] [1,2,5]thiadiazolo[3,4-c]acridine (VII) (65%). The reaction of IV with a mixture of methyl and ethyl 2-oxocyclohexanecarboxylate gave the adduct, which was ring closed in Dowtherm to 7,9,10,1 1-tetrahydro[1,2,5] thiadiazolo[3,4-c]acridin-6(8H)one (VIII) (70%). Chlorination of VIII with phosphorus oxychloride gave 6-chloro-7,8,9,10-tetrahydro[1,2,5]thiadiazolo[3,4-c]acridine (IX) (84%), which was condensed with 3-(dimethylamino)-1-propanethiol hydrochloride in phenol yielding 6-[ [3-(dimethylamino)propyl]thio]-7,8,9,10-tetrahydrof 1,2,5]-thiadiazolo[3,4-c]acridine (X) (27%). 6-[ [3(1)imethylamino)propyl]thio]-8,9-dihydro-7H-cyclopenta[b] [1,2,5]thiadiazolo[3,4-h]quinoline (XIII) (25%) was prepared similarly from IV and a mixture of methyl and ethyl 2-oxocyclopentanecarboxylate via 7,8,9,10-tetrahydro-6H-cyclopenta[b][1,2,5]thiadiazolo[3,4-h]quinolin-6-one (XI) (85%) and 6-chloro-8,9-dihydro-7H-cyclopenta[b][1,2,5]thiadiazolof3,4-h]quinoline (XII) (56%). The effects of compounds VII-XIII as inhibitors of platelet aggregation are discussed. 相似文献
4.
Jasmina S. Brbori? Sote Vladimirov Mirjana S. Jovanovi? Nikola Dogovi? 《Monatshefte für Chemie / Chemical Monthly》2004,28(11):1009-1014
The synthesis and characterization of N-[2-[[4-iodo-2,6-bis(1-methylethyl)phenyl]amino]-2-oxoethyl]-N-(carboxymethyl)glycine and N-[2-[(4-iodo-2,6-diethylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine is presented, as well as a modified and improved synthesis of N-[2-[(2,4-diiodo-6-methylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine. These compounds are new agents for hepatobiliary imaging. 相似文献
5.
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
6.
Summary. The synthesis and characterization of N-[2-[[4-iodo-2,6-bis(1-methylethyl)phenyl]amino]-2-oxoethyl]-N-(carboxymethyl)glycine and N-[2-[(4-iodo-2,6-diethylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine is presented, as well as a modified and improved synthesis of N-[2-[(2,4-diiodo-6-methylphenyl)amino]-2-oxoethyl]-N-(carboxymethyl)glycine. These compounds are new agents for hepatobiliary imaging. 相似文献
7.
Giuseppe Daidone Salvatore Plescia Jole Fabra 《Journal of heterocyclic chemistry》1980,17(7):1409-1411
Thermal decomposition of the diazonium sulfate derived from N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-aminobenzamide afforded products formulated as 1-phenyl-3-methyl[2]benzopyrano[4,3-c]pyrazol-5-one (yield 10%), 1,4-dimethyl-3-phenylpyrazolo[3,4-c]isoquinolin-5-one (yield 10%), N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-hydroxybenzamide (yield 8%) and 4′-hydroxy-2,3′-dimethyl-1′-phenylspiro[isoindoline-1,5′-[2]-pyrazolin]-3-one (yield 20%). Decomposition of the diazonium sulfate derived from N-methyl-(1,3-diphenylpyrazol-5-yl)-2-aminobenzamide gave products formulated as 7,9-dimethyldibenzo[e,g]pyrazolo[1,5-a][1,3]-diazocin-10-(9H)one (yield 8%), 4-methyl-1,3-diphenylpyrazolo[3,4-c]isoquinolin-5-one (yield 7%) and 4′-hydroxy-2-methyl-1′,3′-diphenylspiro[isoindoline-1,5′-[2]pyrazolin]3-one (yield 10%). The spiro compounds 6a,b underwent thermal and acid-catalysed conversion into the hitherto unknown 2-benzopyrano[4,3-c]pyrazole ring system 7a,b in good yield. Analytical and spectral data are presented which supported the structures proposed. 相似文献
8.
Yoshihisa Kurasawa Noriko Yoshishiba Tomomi Kureyama Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1993,30(4):1149-1152
The reaction of 7-chloro-4-(2-cyano-2-hydroxyvinyl)tetrazolo[1,5-a]quinoxaline 2a with o-aminophenol gave 7-chloro-4-(b-hydroxyphenylcarbamoylmethylene)4,5-dihydrotetrazolo[1,5-a]quinoxaline 4 , while the reaction of compound 2a with o-aminophenol hydrochloride afforded 4-[2-(2-benzoxazolyl)-2-hydroxyvinyl]-7-chlorotetrazolo[1,5-a]quinoxaline 5 , whose acetylation provided 4-[2-acetoxy-2-(2-benzoxazolyl)vinyl]-7-chlorotetrazolo[1,5-a]quinoxaline 6 . The behavior in a deuteriodimethyl sulfoxide or deuteriotrifluoroacetic acid solution is described for compounds 4–6 . 相似文献
9.
Y. H. R. Jois C. D. Kwong J. M. Riordan J. A. Montgomery J. A. Secrist 《Journal of heterocyclic chemistry》1993,30(5):1289-1292
Ribosylation of 3-amino-5H-[1,2,4]triazolo[4,3-b][1,2,4]triazole ( 1 ) with l-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose and stannic chloride resulted in the following protected nucleoside analogs: 3-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)[1,2,4]triazolo[4,3-β][1,2,4]triazole ( 4 ), 3-amino-1-(2,3,5-tri-O-benzoyl-α-D-ribofuranosyl)[1,2,4]triazolo[4,3-β][1,2,4]triazole ( 5 ), 3-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)[1,2,4]triazolo[4,3-β][1,2,4]triazole ( 5 ), and 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl) amino-5H-[1,2,4]triazolo[4,3-b]-[1,2,4]triazole ( 7 ). Compounds 4–6 were deprotected to 3-amino-1-β-D-ribofuranosyl[1,2,4]triazolo[4,3-b][1,2,4]-triazole ( 3 ), 3-amino-1-α-D-ribofuranosyl[1,2,4]triazolo[4,5-b][1,2,4]triazole ( 8 ), and 3-imino-2H-2-β-D-ribo-furanosyl[1,2,4]triazolo[4,3-b][1,2,4]triazole ( 9 ), while 7 could not be deprotected without decomposition. Compounds 1, 4, 6, 7 , and 9 were screened and found to have no antiviral activity. 相似文献
10.
A. Yu. Tyurin A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2009,58(1):212-215
Thermolysis of 7-azido-8-(2H-1,2,3-triazol-2-y1)-1,2,3,4-benzotetrazine 1,3-dioxide and 7-azido-8-(l H-1,2,3-triazol-l-yl)-1,2,3,4-benzotetrazine 1,3-dioxide afford new heterocyclic systems, viz., 7,11-dehydro-7H, 11H [1,2,3]triazolo[l′,2′:2,3][1,2,3]triazolo[4,5-f]-[1,2,3,4]benzotetrazine 1,3-dioxide and 7,9-dehydro-7 H, 9H [1,2,3]triazolo[2′,1′:2,3]-[1,2,3]triazolo[4,5-f][1,2,3,4]benzotetrazine 1,3-dioxide, respectively, and their thermal stability has been studied. 相似文献
11.
Yu. L. Zborovskii V. V. Orysyk V. I. Staninets V. V. Bon’ 《Russian Journal of Organic Chemistry》2011,47(6):881-885
Cyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione by the action of iodine, bromine, or sulfuryl chloride gave 2-(2-{4-[4,5-dihydro-5-(halomethyl)-thiazol-2-yl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione hydrohalides which were converted into 2-{2-[4-(5-methylthiazol-2-yl)piperazin-1-yl]ethyl}-1H-benzo[de]isoquinoline-1,3(2H)-dione. 相似文献
12.
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
13.
Yoshihisa Kurasawa Tomomi Kureyama Noriko Yoshishiba Ritsuko Katoh Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1993,30(2):537-541
The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 8 with furfural, 3-methyl-2-thiophene-carbaldehyde, 2-pyrrolecarbaldehyde, 4-pyridinecarbaldehyde and pyridoxal hydrochloride gave 6-chloro-2-[2-(2-furylmethylene)-1-methylhydrazino]quinoxaline 4-oxide 5a , 6-chloro-2-[1-methyl-2-(3-methyl-2-thienyl-methylene)hydrazino]quinoxaline 4-oxide 5b , 6-chloro-2-[1-methyl-2-(2-pyrrolylmethylene)hydrazino]quinoxa-line 4-oxide 5c , 6-chloro-2-[1-methyl-2-(4-pyridylmethylene)hydrazino]quinoxaline 4-oxide 5d and 6-chloro-2-[2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridylmethylene)-1-methylhydrazino]quinoxalme 4-oxide 5e , respectively. The reaction of compound 5a or 5b with 2-chloroacrylonitrile afforded 8-chloro-3-(2-furyl)-4-hydroxy-1-methyl-2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline-5-carbonitrile 6a or 8-chloro-4-hydroxy-1-methyl-3-(3-methyl-2-thienyl)-2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline-5-carbonitrile 6b , respectively, while the reaction of compound 5e with 2-chloroacrylonitrile furnished 11-chloro-7,13-dihydro-4-hydroxy-methyl-5,14-methano-1,7-dimethyl-16-oxopyrido[3′,4′:9,8][1,5,6]oxadiazonino[3,4-b]quinoxaline 7. 相似文献
14.
Treatment of 5-methylthio-2,3-dihydrothieno[3,2-f]-1,4-thiazepine ( 9 ) with acylhydrazines gave 5,6-dihydrothieno[3,2-f]-1,2,4-triazolo[4,3-d][1,4]thiazepines 10, 11 , and that of 9 with ethyl anthranilate gave 5,6-dihydrothieno[3′,2′:6,7][1,4]thiazepino[5,4-b]quinazolin-8-one ( 14 ). Reaction of 9 with hydrazine hydrate or 4-chlorophenylhydrazine afforded 5-hydrazino compounds 12, 15 , which were subsequently cyclized to ethyl 5,6-dihydrothieno[3,2-f]-1,2,4-triazolo[4,3-d][1,4]thiazepine-3-carboxylate ( 13 ), 2-(4-chlorophenyl)-5,6-dihydrothieno[3,2-f]-1,2,4-triazolo[4,3-d][1,4]thiazepin-3(2H)-one ( 16 ) and 2-(4-chlorophenyl)-6,7-dihydro-2H-thieno[3,2-f][1,2,4]triazino[4,3-d][1,4]thiazepine-3,4-dione ( 17 ). New thieno-anellated heterocycles were prepared with the aim of studying their affinity for the benzodiazepine receptors. 相似文献
15.
Guanidine transforms the following: (a) 3-formylchromone into a mixture of 2-amino-5-(2-hydroxybenzoyl)pyrimidine and 2-amino-5H-[1]-benzopyrano[4,3-d]pyrimidine; (b) the diacetate of 3-methylidyne-chromone into 2-amino-5-hydroxy-5H-[1]benzopyrano[4,3-d]pyrimidine; and (c) the oxime of 3-formylchromone into 2-amino-5H-[1]benzopyrano-[4,3-d]pyrimidin-5-one. Thiourea, acetamidine and nitroguanidine can also generate pyrimidines of the same type with 3-formylchromone, the diacetate of 3-methylidynechromone or 3-(1,3-dioxolan)chromone. 相似文献
16.
Colette Deschamps-Vallet Michle Meyer-Dayan Jean Andrieux Jacques Riboulleau Bernard Bodo Darius Molho 《Journal of heterocyclic chemistry》1977,14(3):489-492
5-Oxo-5H,7H-[2]benzopyrano[4,3-b][1]benzopyran ( 2 ) has been synthesized from 3-(o-hydroxybenzylidene)isochroman-1,4-dione ( 3 ) by reductive cyclization, and from 5H,7H[2]benzo-pyrano[4,3-b][1]benzopyran-5,7-dione ( 4 ) by selective hydro-genation. This second method affords the dihydro compound 6 or 6a,12a-dihydro-5H,7H-[2]benzopyrano[4,3-b] [1 ]benzopyran-5-one as reaction time increases. 相似文献
17.
Syntheses of (±)-2-exo-cyano-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-endo-yl acetate ( 1 ) and of (±)-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-one ( 2 ) are reported. The additon of PhSeCl to 1 afforded (±)-5-endo-chloro-2-exo-cyano-1-methyl-6-exo-(phenylselenenyl)-7-oxabicyclo[2.2.1]hept-2-endo-yl acetate ( 6 ), whereas 2 added to PhSeCl with the opposite regioselectivity giving (±)-6-endo-chloro-1-methyl-5-exo-(phenylselenenyl)-7-oxabicyclo[2.2.1]heptan-2-one ( 7 ). These adducts were converted into 5-chloro-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-one ( 9 ) and 6-chloro-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-one ( 10 ), respectively. 相似文献
18.
Ibrahim Narin Salih Sarioglan Beril Anilanmert Hayati Sari 《Journal of solution chemistry》2010,39(10):1582-1588
The pK
a constants and relative abundances of unionized and ionized forms of Montelukast sodium {the sodium salt of 2-[1-[[(1R)-1-[3-[2-(7-chloroquinolin-2-yl)ethenyl] phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetic
acid} and Levodropropizine {(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol} were determined potentiometrically from measurements at various pHs. These determinations
were in order to relate their pK
a values with their bioavailability and to provide chemical data to be used in their analysis. 相似文献
19.
Srihari Kusuma W. David Wilson David W. Boykin 《Journal of heterocyclic chemistry》1985,22(5):1229-1232
A series of five 8-substituted α-[bis(2-hydroxyethyi)aminoethyl]naphtho[2,1-b]thiophenes 7 and a series of seven N-(3-dimethylaminopropyl)-8-substituted naphtho[2,1-b]thiophene-4-carboxamides 8 have been synthesized. The naphtho[2,1-b]thiophene-4-carboxylic acids 4 were prepared by photooxidative cyclization of α-(2-thienyi)-β-arylacrylic acids 3. The carboxylic acids 4 were converted by a conventional five step route involving α-bromoketone intermediates to the a-[bis(2-hydroxyethyl)aminomethyl]-8-substituted naphtho-[2,1-6]thiophene-4-methanols 7 and by a standard two-step amide preparation to the N-(3-dimethylaminopropyl)-8-substituted naphtho[2,1-6]thiophene-4-carboxamides 8 . 相似文献
20.
A. V. Sergievskii O. A. Krasnoshek S. F. Mel'nikova I. V. Tselinskii 《Russian Journal of Organic Chemistry》2002,38(6):872-874
Reactions of 4-aminofurazan-3-carboxylic acid iminoester with o-aminophenol and ethylenediamine give rise respectively to 4-(1,3-benzoxazol-2-yl)- and 1-(4,5-dihydro-1H-imidazol-2-yl)-1,2,5-oxadiazol-3-amines, with aminoethanol arises 2-[(Z)-1-amino-1-(4-amino-1,2,5-oxadiazol-3-yl)methylideneamino]-1-ethanol. Treating of 3-amino-4-(1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazole with triethyl orthoformate in acetic anhydride yielded benzo[4,5]imidazo[1,2-c][1,2,5]oxadiazolo[3,4-e]pyrimidine, and alkylation with haloalkanes furnished 3-amino-4-(1-R-benzo[d]imidazol-2-yl)-1,2,5-oxadiazoles. 相似文献