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1.
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
2.
Syntheses of 5H-[1,2,4]triazolo[5′,1′:2,3][1,3]thiazino[5,4-c]quinolines 8, 5H-[1,2,4]triazolo[3′,4′:2)3][1,3]thiazino[5,4-c]quinolines 9, 5H-[1,2,4]triazolo[5′,1′:2,3][1,3]thiazino[5,6-c]quinolines 14 and 5H-[1,2,4]triazolo[3′,4′:2,3][1,3]thiazino[5,6-c]quinolines 15 are described starting from 4-chloro-3-chloromethylquinaldine (4) and 1,2,4-triazole-5-thiols 5 taking advantage of different reactivity of the chlorine atoms of 4 under different reaction conditions. The structures of products 8, 9, 14 and 15 and the intermediates leading to them were confirmed by desulfurization, unequivocal syntheses and nmr spectroscopy as well. 相似文献
3.
Mnika Szab Jzsef Kksi Lszl
rfi Attila Kovcs Istvn Hermecz 《Journal of heterocyclic chemistry》1997,34(1):21-25
3H,7H-[1,4]Diazepino[3,4-b]quinazolone-3,7-diones 9, 11 were synthesized starting from 2-(1-bromo-ethyl)quinazolin-4(3H)-ones 3 and 17 via 2-[1-(4-methoxyphenylamino)ethyl]quinazolin-4(3H)-ones 4 and 18. Cyclization of 3-[2-(1-bromoethyl)-4-oxo-3,4-dihydroquinazolin-3-yl)propionic acid 14 by the action of triethylamine provided the first representative of the tricyclic 7H-[1,4]oxazepino[3,4-b]quinazoline-3,7-dione system, compound 15. The new tricyclic derivatives 9, 11 and 15 are characterized by uv, ir and 1H nmr spectroscopy. 相似文献
4.
Charles A. Lovelette 《Journal of heterocyclic chemistry》1979,16(3):555-560
A convenient synthesis of 3-amino-6-hydrazino-5(2H)[1,2,4]triazinone 4 has been developed and a study of the reactions of 4 with aliphatic acids, orthoesters and miscellaneous active carbonyl reagents has been undertaken. When 4 was refluxed in either neat acid or orthoester in dimethylformamide, a facile ring closure reaction with the N-1 nitrogen of the 1,2,4-triazine ring occurs affording a novel series of 3-aIkyl(aryl)-8(5H)-s-triazolo[3,4-f] [1,2,4]triazinones ( 6–11 ). Ring closure with carbon disulfide and cyanogen bromide is also reported affording 6-amino-3(2H)thio-8(5H)-s-triazolo[3,4-f] [1,2,4]triazinone 12 and 3,6-diamino-8(5H)-s-triazolo-[3,4-f] [1,2,4]triazinone 14 , respectively. In addition 4 has been converted into 3-amino-6-azido-5(2H)-1,2,4-triazinone 15 which was employed in a study of azide-tetrazole equilibrium affording 6-amino-8(5H)tetrazolo[1,5-f][1,2,4]triazinone 16 . Rates for interconversion at various temperatures were measured and an activation energy for the process determined. 相似文献
5.
1,4-Cycloaddition of dichloroketene to a number of N,N-disubstituted (E)-4-amino methylene-3,4-dihydro-[1]benzothiepin-5(2H)-ones gave in excellent yield N,N-disubstituted 4-amino-3,3-dichloro-3,4,5,6-tetrahydro-2H-[1]benzothiepino[5,4-b]pyran-2-ones III, which are derivatives of the 2H-[1]benzothiepino[5,4-b]pyran system. Dehydrochlorination of III with DBN afforded N,N-disubstituted 4-amino-3-chloro-5,6-dihydro-2H-[1]-benzothiepino[5,4-b]pyran-2-ones, generally in excellent yield. 相似文献
6.
Silvio Massa Giorgio Stefancich Marino Artico Federico Corelli 《Journal of heterocyclic chemistry》1984,21(6):1877-1880
The synthesis of derivatives of 1H,4H-pyrazolo[4,3-f]pyrrolo[1,2-a][1,4]diazepine, a new tricyclic nitrogen-containing nucleus is reported. Condensation of arylaldehydes with 4-aminomethyl-1-phenyl-5-(1-pyrryl)pyrazole afforded the title compounds. Bischler-Napieralski intramolecular cyclization of 4-acetamidomethyl-1-phenyl-5-(1-pyrryl)pyrazole was also studied. The reaction led to 6-methyl-1-phenyl-1H,4H-pyrazolo[4,3-f]pyrrolo[1,2-a][1,4]diazepine or alternatively to 4-chloromethyl-1-phenyl-5-(1-pyrryl)pyrazole depending on the solvent used. 相似文献
7.
Steven L. Castle Phillip J. Buckhaults Larry J. Baldwin J. Dew McKenney Raymond N. Castle 《Journal of heterocyclic chemistry》1987,24(4):1103-1108
A series of monomethoxy[1]benzothieno[2,3-c]quinolines 24-28 were prepared by photocylization of the appropriate 3-chloro-N-phenylbenzo[b]thiophene-2-carboxamides 9–13 to [1]benzothieno[2,3-c]quinolin-6(5H)-ones 14-18 followed by chlorination to 6-chloro[1]benzothieno[2,3-c]quinolines 19-23 then dechlorination resulting in the title compounds except for 25 which was achieved by direct reduction of 15 . Reaction of 24-28 with methyl iodide provided the corresponding N-methyl quaternary salts 29-33 . Also, conversion of 4-meth-oxy[1]benzothieno[2,3-c]quinolin-6(5H)-one 16 to 4-methoxy-6-methylthio[1]benzothieno[2,3-c]quinoline 35 and 4,6-dimethoxy[1]benzothieno[2,3-c]quinoline 36 is described. 相似文献
8.
Piergiorgio Pecorari Marcella Rinaldi M. Paola Costi Luciano Antolini 《Journal of heterocyclic chemistry》1992,29(6):1449-1455
Derivatives of two new molecular structures, namely, 7,8-dihydro-6H,10H-[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazin-10-one and 6,7-dihydro-9H-thiazolo[3,2-a][1,2,5]thiadiazolo[3,4-d][pyrimidin-9-one, and derivatives of N-substituted sulfamic acid, namely, (8-amino-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-on-7-yl)sulfamic acid and (7-amino-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-on-6-yl)sulfamic acid, were separated out as by-products in the reduction reaction of 8-amino-3,4-dihydro-7-nitroso-2H,6H-pyrimido[2,1- b][1,3]thiazin-6-one and 7-amino-2,3-dihydro-6-nitroso-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives, respectively, with sodium hydrosulfite. A mechanism of reaction, which hypothesizes the action of sodium hydrosulfite in an asymmetic form, is proposed. The results of single-crystal X-ray investigation on 7,8-dihydro-6H,10H-[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazin-10-one (R = 0.032 for 863 reflections) and (8-amino-3,4-dihydro-2H,6H-pyrimido[2,1-b]- [1,3]thiazin-6-on-7-yl)sulfamic acid, sodium salt (R = 0.028 for 3507 reflections) are reported. 相似文献
9.
Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones. I. 3-unsubstituted compounds
David T. Connor Paul C. Unangst Charles F. Schwender Roderick J. Sorenson Mary E. Carethers Chester Puchalski Richard E. Brown 《Journal of heterocyclic chemistry》1984,21(5):1557-1559
Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones via a Pechmann condensation of 3-carbethoxy-1-methyl-4-piperidone with various phenols is described. The limitations of this method are discussed. Synthesis of the parent ring system 3a via reduction of 1,2,3,4-tetrahydro-3-(phenylmethyl)-8-[(1-phenyl-1H-tetrazol-5-yl)oxy]-5H-[1]benzopyrano[3,4-c]pyridin-5-one ( 5 ) is also described. 相似文献
10.
Vas’kevich R. I. Bentya A. V. Staninets V. I. 《Russian Journal of Organic Chemistry》2010,46(2):286-290
The reaction of 1-(4-oxo-1-R-5H-pyrazolo[3,4-d]pyrimidin-6-yl)-4-arylthiosemicarbazides with methyl iodide gave rise to 1,2,4-triazolo-pyrazolopyrimidinones of linear structure,
and with dicyclohexylcarbodiimide the products had angular and linear structure. The heating of compounds obtained higher
than their melting point resulted in their isomerization into 7-aryl-amino-1-R-1,8-dihydro-4H-pyrazolo[3,4-d]-[1,2,4]triazolo[1,5-a]pyrimidin-4-ones. 相似文献
11.
Piergiorgio Pecorari Marcella Rinaldi Maria Paola Costi 《Journal of heterocyclic chemistry》1989,26(6):1701-1705
Derivatives of two new molecular structures, namely, [1,3]thiazino[3,2-a]purine and [1,2,3]triazolo[4,5-d]-[1,3]thiazino[3,2-a]pyrimidine, were synthesized together with other heterocyclic compounds. Retrosynthetic analysis of their molecular skeletons suggested a simple way of obtaining 3,4-dihydro-7,8-diamino-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one, which is a useful intermediate for their synthesis. This intermediate and the thiazole homologue were obtained directly by reaction of 5,6-diamino-2,3-dihydro-2-thioxo-4(lH)-pyrimidi-none with 1,3- or 1,2-dibromoalkane, respectively. 相似文献
12.
David T. Connor Patricia A. Young Maximilian Von Strandtmann 《Journal of heterocyclic chemistry》1981,18(4):697-702
3-Aminochromone and 3-aminocoumarin were condensed with diethyl ethoxymethylenemalonate and with dimethyl acetylenedicarboxylate to give intermediates, which were thermally cyclized to give 4,10-dihydro-4,10-dioxo-lH-[1]-benzopyrano[3,2-b]pyridinecarboxylates and 1,5-dihydro-1,5-dioxo-4H-[1]-benzopyrano-[3,4-b]pyridinecarboxylates. 2-Aminochromone was converted to 4,5-dihydro-4,5-dioxo-1H-[1]-benzopyrano-[2,3-b]pyridinecarboxylate via an intermediate condensation product with diethyl ethoxymethylenemalonate. These esters were hydrolyzed to the corresponding carboxylic acids (21, 30, 36, 50, and 60). Attempts to prepare 4,5-dihydro-4,5-dioxo-1H-[1]-benzopyrano[4,3-b]pyridinecarboxylates from 4-aminocoumarin were unsuccessful. 相似文献
13.
Maria C. Aversa Paola Bonaccorsi Placido Giannetto David A. Leigh 《Journal of heterocyclic chemistry》1989,26(6):1619-1622
New heterotricyclic systems, 6,10a,11,11a-tetrahydro-5H-bis[1,2,4]oxadiazolo[4,5-d:5′,4′-g][1,4]diazepines 6,7,9-11 and 5,6,10,10a,11,11a-hexahydro-1H-bis[1,2,4]triazolo[4,3-d:3′,4′-g][1,4]diazepines 8,12 have been obtained by double site- and regie-specific 1,3-dipolar cycloaddition of mesitylnitrile oxide ( 1 ) or diphenylnitrile imine ( 2 ) to 5,7-disubstituted 2,3-dihydro-1H-1,4-diazepines 3-5. The structure of the synthesized bis-adducts 6-12 shows that the hetero double bonds are much more reactive than the olefinic ones in the dipolarophiles under study. No evidence for the formation of mono-adducts was obtained. 相似文献
14.
Thirteen 1-(9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-yl)-3-alkylaminoazetidines 11 have been synthesized in three steps from 4-amino-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene ( 6 ), which was obtained from the reduction of either 4-azido 4 or 4-hydroxyimino 5 derivatives. All the compounds have been evaluated as potential antidepressive agents. 相似文献
15.
Michel Boulouard Patrick Dallemagne Abdellah Alsaïdi Sylvain Rault 《Journal of heterocyclic chemistry》1996,33(6):1743-1749
Treatment of 3-(2-formyl-1H-pyrrol-1-yl)-2-thiophenecarboxamide by various nucleophiles like methyl ketones, amines, alcohols, thiols or acetates led to new 5,6-dihydro-4H-pyrrolo[1,2-a]thieno-[2,3-f][1,4]diazepines. 相似文献
16.
Sylvain Rault Michel Cugnon De Svricourt Paulette Touzot Max Robba Hussein El-Kashef 《Journal of heterocyclic chemistry》1980,17(7):1399-1404
The nitration and bromination of both [1]benzothieno[3,2-d]pyrimidin-4(3H)one ( 1 ) and [1]benzothieno-[3,2-d]pyrimidine ( 2 ) has been studied. Nitration of 1 at ?30° afforded a mixture of 8-nitro[1]benzothieno-[3,2-d]pyrimidin-4(3H)one ( 7b ) (70%) and 6-nitro[1]benzothieno[3,2-d]pyrimidin-4(3H)one ( 7a ) (30%). However when the nitration was carried out at 60°, the 6,8-dinitro derivative 8 was the result. On the contrary, the nitration of 2 at ?30° gave a single nitration product, 8-nitro[1]benzothieno[3,2-d]pyrimidine ( 11 ). The bromination of both 1 and 2 gave the corresponding 8-bromo derivatives 10 and 13 . Assignment of structure of all the products was based on ir and nmr spectral studies and on unequivocal syntheses. 相似文献
17.
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
18.
5-Hydroxy-7-alkyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitriles (VIIb-d) and 5-hydroxy-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, ethyl ester (VIIa) were prepared from 5-carbethoxy-4-chloro-2-phenylpyrimidine (IV) via 4-[(cyanomethyl)alkylamino[-2-phenyl-5-pyrimidinecarboxylic acid, ethyl esters (Vb-d) and 4-[(carboxymethyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid, diethyl ester (Va), respectively. The hydroxy group of the pyrrolo-[2,3-d]pyrimidines could be methylated, acetylated and tosylated. Hydrolysis of 5-methoxy-7-methyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile (IX) afforded the corresponding amide (X). 相似文献
19.
7-Amino-2H,4H-vic-triazolo[4,5-c][1,2,6]thiadiazine 5,5-dioxide was prepared by two different ways from 3,4,5-triamirio-1,2,6-lhiadiazine 1, 1-dioxide and 3,5-diamino-4H-1,2,6-thia-diazine 1, 1-dioxide respectively. 7-A:nino-2-phenyl-4H-vic-triazolo[4,5-c] [1,2,6]thiadiazine 5,5-dioxide was obtained by lead telraacetate oxidation of 3,5-diamino-4-phenylazo-1, 2, 6-thiadiazine 1, 1-dioxide. 相似文献
20.
The substitution and addition reactions of the 2H[1]benzothiéno[2,3-d]phyridazinethione-1 and the 3H[1]benzothiéno[2,3-d]pyridazinethione-4 gave N- or S-substituted derivatives whose structures were identified by 1R and NMR spectroscopy. 相似文献