共查询到20条相似文献,搜索用时 31 毫秒
1.
Shih-Fong Chen Raymond P. Panzica Daniel L. Dexter Ming-Yu Wang Chu Paul Calabresi 《Journal of heterocyclic chemistry》1982,19(2):285-288
Certain 4-alkylamino and 4-arylalkylamino derivatives of the imidazo- and v-triazolo[4,5-d]pyridazine ring systems were prepared and evaluated against two human colon carcinomas (DLD-1 and HCT-15) and one human lung carcinoma (LX-1), in vitro. 4-Methylthioimidazo[4,5-d]pyridazine ( 1 ) and 4-methylthio-v-triazolo-[4,5-d]pyridazine ( 9 ) served as precursors to the title compounds. Treatment of these heterocycles with the appropriate amine (ammonia, methylamine, dimethylamine, benzylamine and hydrazine) provided the desired derivatives of that ring system. 4-AIP ( 2 ) and 2-aza-4-AIP ( 10 ) served as precursors to the 4-dimethylaminomethyleneamino derivatives 6 and 14 , respectively. Likewise, the 4-hydrazino analogs ( 7 and 15 ) served as intermediates in the syntheses of benzaldehyde-p-[bis(2-chloroethyl)amino]amino[4,5-d]-pyridazin-4-yl-hydrazone ( 8 ) and benzaldehyde-p-[bis(2-chloroethyl)amino]amino-v-triazolo[4,5-d]pyridazin-4-yl-hydrazone ( 16 ), respectively. 相似文献
2.
Several pyridazines have been prepared as intermediates in the synthesis of monosubstituted imidazo[4,5-d]pyridazines, monosubstituted v-triazoIo[4,5-d]pyridazines and monosubstituted pyrazino [2,3d] pyridazines. The new ring system, 7H-imidazo[4,5-d]tetrazolo[l,5-b] pyridazine (XIV) has been prepared unsubstituted. Furthermore, unsubstituted imidazo[4,5-d]pyridazine (XI) has been prepared. Calculations for XI and XIV were made by approximate SCF LCAO-MO with CNSO II theory. 相似文献
3.
Robert A. Long John F. Gerster Leroy B. Townsend 《Journal of heterocyclic chemistry》1970,7(4):863-869
The synthesis of 7-methylpyrazolo[4,3-d]-v-triazin-4-one ( 6 ), a derivative of the new ring system, pyrazolo[4,3-d]-v-triazine, has been accomplished by a diazotization reaction. Ring closure of the appropriate pyrazole derivative and oxidation of the preformed bicyclic heterocycle with m-chloroperoxybenzoic acid has furnished 7-substituted 3-methylpyrazolo[4,3-d]pyrimidine 6-oxides. Ring closures to yield various 5,7-disubstituted 3-methylpyrazolo[4,3-d]pyrimidines are also discussed. 相似文献
4.
Starting from readily available methyl 2-substituted4-methyl-5-thiazolyl ketone and methyl 4-methyl-2-phenyl-5-selenazolyl ketone, thieno[3, 4-d]thiazole, thieno[3, 4-d]selenazole, selenolo[3, 4-d]thiazole and selenolo[3, 4-d]selenazole were prepared. The structures of all compounds were confirmed by analytical and spectroscopic methods. 相似文献
5.
3H-benzothieno[3,2-d]pyrimidin-4-one (3) was synthesized by bimolecular cyclising the 3-amino-2-carbethoxybenzothiophene (1) with formamide. The electrophilic substituion of 3 afforded N-methylated lactam derivavtives, the structure of which was assigned by 'H nmr and unequivocal synthesis. The sysnthesis of benzothieno[3,2-d]pyrimidine (7) was achieved by desulphurization of the 3H-benzothieno[3,2-d]-[3,2-d]pyrimisine-4-thione (6) or by oxydation of the 4-hydrazinobenzothieno[3,2-d]primidine (5). 相似文献
6.
Yasumitsu Tamura Joong-Hyup Kim Yasuyoshi Miki Hironori Hayashi Masazumi Ikeda 《Journal of heterocyclic chemistry》1975,12(3):481-483
New routes to the v-triazolo[1,5-a]pyridine and pyrazolo[1,5-a]pyridine ring systems are described. Treatment of the N-amine salts of 2-picolinealdehyde oxime or 2-pyridyl ketone oximes with polyphosphoric acid gave v-triazolo[1,5-a]pyridines in fair yields. Treatment of 2-picolyl ketones or their oximes with O-mesitylenesulfonylhydroxylamine produced directly pyrazolo-[1,5-a]pyridines. These reactions were extended to the quinoline cases. 相似文献
7.
The synthesis of 4-(3,5-dimethylpyrazol-1-yl)-v-triazolo[4,5-d]pyridazine, 4-(3,5-dimethylpyrazol-1-yl)imid-azo[4,5-d]pyridazine and several S-substituted derivatives of 4-(3,5-dimethylpyrazol-1-yl)imidazo[4,5-d]pyrid-azine-2-thiol is reported. These syntheses were carried out to provide a variety of interesting compounds for biological screening. 相似文献
8.
The parent imidazo[4,5-c]pyridazine (IV) has been prepared for the first time by three different routes. 1-Methylimidazo[4,5-c]pyridazine (XX) and 3-methylimidazo[4,5-c]pyridazine (XXVII) have been prepared by unequivocal syntheses. The constitution of the methylation product of imidazo[4,5-c]pyridazine-2-thiol (VIII) has been shown to be 2-methylthioimidazo[4,5-c]-pyridazine (IX) by the unequivocal syntheses of 1-methylimidazo[4,5-c]pyridazine-2-thiol (XXIII) and 3-methylimidazo[4,5-c]pyridazine-2-thiol (XXXIII). Likewise, the structure of the methylation product (XIII) was shown to be S-methylation by the unequivocal syntheses of 1-methyl-2-methylthio-6-chloroimidazo[4,5-c]pyridazine (XXIV) and 3-methyl-2-methylthio-6-chloroimidazo[4,5-c]pyridazine (XXXI), respectively. Several 7-substituted amino-v-triazolo-[4,5-c]pyridazines (XXXVIII) have been prepared from 7-chloro-v-triazolo[4,5-c]pyridazine (XXXVII). 相似文献
9.
2-o-Chlorophenyl-2H-naphtho[1,2-d]v-triazole-4,5-quinone condenses with semicarbazide and some of its derivatives at the 4 position and the products cyclize into the corresponding 1,2,4-triazines. Reactions of these triazines with some reagents are described. 相似文献
10.
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
11.
Giuliana Biagi Irene Giorgi Oreste Livi Clementina Manera Valerio Scartoni 《Journal of heterocyclic chemistry》1999,36(5):1195-1198
Some new 1,2,3-triazolo[4,5-e]-1,2,4-triazolo[3, 4 -c]pyrimidmes were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyrimidines via the formation of the 1,2,4-triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate to give the expected tricyclic derivatives 7 , 8 and 9 . Intramolecular cyclization of the ethoxycarbonylhydrazino derivatives 10 gave the tricyclic compounds 11 bearing an hydroxyl group in the 3 position. The v-triazolo-s-triazolopyrimidine derivatives were tested towards the A1 and A2A adenosine receptors in binding assays, but they did not show any receptor affinity. 相似文献
12.
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
13.
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
14.
Derek R. Buckle D. James Outred Caroline J. M. Rockell 《Journal of heterocyclic chemistry》1981,18(6):1117-1122
Ethyl 1-benzyl-5-chloro-v-triazole-4-carboxylate ( 3 ) undergoes facile nucleophilic displacement of the halogen atom with phenoxide ion to yield aryloxytriazolecarboxylates 4 which debenzylate under hydrogenolytic conditions to N-H triazoles 7 . Saponification and cyclization with either polyphosphoric acid or phosphoric oxide in methanesulphonic acid leads to the novel 9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole system 9 , members of which have potential as antiasthmatic agents. 相似文献
15.
M. Robba M. Cugnon de Sevricourt J. M. Lecomte 《Journal of heterocyclic chemistry》1975,12(3):525-527
The cyclization reactions of the 4-hydrazinothieno[2,3-d]pyrimidines give s-triazolo[1,2-c]-thieno[3,2-e]pyrimidines and tetrazolo[1,5-c]thieno[3,2-e]pyrimidines. 相似文献
16.
Starting from the readily available 4-bromomethy-5-carbethoxy 1,2,3-thiadiazole (V), 5-bromomethy-4-carbethoxy-1,2,3-thiadiazole (IX) and ethyl 2-aryl-5-bromomethyloxazole-4-carboxylate (XIV), 4,10-dihydro-10-oxo[1]benzoxepino[3,4-d][1,2,3]thiadiazole (Ia), 4,10-dihydro-10-oxo[1]benzothiepino[3,4-d][1,2,3]thiadiazole (Ib), 4,10-dihydro-4-oxo[1]benzothiepino[4,3-d] [1,2,3]thiazole (II), 2-aryl-4,10-dihydro-4-oxo[1]benzoxepino[4,3-d]oxazoles (XIXa-XIXc) and 2-aryl-4,10-dihydro-4-oxo[1]benzothiepino[4,3-d]oxazoles (XIXd-XIXf) were prepared. 相似文献
17.
Hitoxhi Fujimori Yasutaka Kayama Takeshi Hara Kazuhiko Itoh Tamiko Sunami 《Journal of heterocyclic chemistry》1977,14(2):235-240
The synthesis of 4H-pyrrolo[1,2-a]thieno[3,2-f] [1,4]diazepines ( 8 ) is described. Phthal-imidomethylfurans 1 were treated with bromine-methanol to give the dihydrofurans 2 , which were hydrolyzed and then liydrogenated over Raney nickel or with zinc-acetic acid to afford the 1,4-diketones 5 . Condensation of 2-amino-3-benzoylthiophenes 6 with 5 gave 3-benzoyl-2-pyrrolylthiopenes 7 . The removal of the phthaloyl group from 7 with hydrazine hydrate and ring closure to the diazepine ring yielded the new heterocycles 8 . 相似文献
18.
Starting from the readily available ethyl 2-phenyl-4-methyl-thiazole-5-carboxylate (III), 2-phenyl-4-chloromethyl-thiazole (VIII) and 2-aryl-4-chloromethylselenazole (XIV), 2-phenyl-4,10-dihydro-10-oxo-[1]benzoxepino[3,4-d]thiazole (Ia), 2-phenyl-4,10-dihydro-10-oxo[1]benzothiepino[3,4-d]thiazole (Ib), 2-aryl-4,10-dihydro-10-oxo[1]benzoxepino[3,4-d]selenazoles (IIa-IIe) and 2-aryl-4,10-dihydro-10-oxo[1]benzothiepino[3,4-d]selenazoles (IIf-IIj) were prepared. 相似文献
19.
Marjo Merslavi
Andrej Petri
Branko Stanovnik Miha Tiler 《Journal of heterocyclic chemistry》1989,26(3):581-583
The transformations of 7-methyl-7H- and 8-methyl-8H-pyrazolo[4, 3-d]tetrazolo[1, 5-b]pyridazines 1, 2, 9 and 10 into 8-methyl-8H- and 9-methyl-9H-pyrazolo[3, 4-H]-s-triazolo[4, 3-b]pyridazines 7 and 8 , and 1-methyl-1H-and 2-methyl-2H-imidazo[1, 2-b]pyrazolo[3, 4-d]pyridazines 13 and 14 are described. 相似文献
20.
Syntheses of substituted pyrazolo[3,4-b]quinolines, 3,4-dihydro-4-oxopyriraido[4′,5′:4,5]theino[2,3-b]quinoline and 12-phenylpyrido[1′,2′:1,2[pyrimido[4,5-b]quinoline are described. 相似文献