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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.
The o-diamine, 3,4-diamino-1,2,5-thiadiazole ( 2 ), was synthesized from 3,4-dichloro-1,2,5-thiadiazole ( 3 ) hy three methods. Aqueous glyoxal cyclized 2 into [1,2,5]thiadiazolo[3,4–6]-pyrazine ( 14 ). 3,4-Dichloro-1,2,5-thiadiazole 1,1-dioxide ( 18 ) reaeted with 2 to give 1,3-dihydro-bis[1,2,5]thiadiazolo[3,4-b:3′,4′-e]pyrazine 2,2-dioxide ( 19 ). The reaction of 2 with selenium oxyehloride led to [1,2,5]selenadiazolo[3,4-c] [1,2,5]thiadiazole ( 12 ). Ring closure of 2,3-diaminoquinoxaline ( 4 ) with thionyl chloride or selenium oxychloride gave [1,2,5]thiadiazolo-[3,4-b]quinoxaline ( 21 ) and [1,2,5]selenadiazolo[3,4-b]quinoxaline ( 22 ), respectively. Sulfurous acid reduced 21 to the 4,9-dihydro derivative 23 , which was reoxidized to 21 with chloranil. Aqueous hase hydrolyzed 21 to 4 via the hydrated intermediate 24 . Aqueous glyoxal cyclized 4 to the covalent hydrate of pyrazino[2,3-b]quinoxaline ( 26 ), 27 , which was dehydrated to 26 . Compound 26 underwent rapid addition of two alcohols in a process analogous to covalent hydration. 相似文献
3.
Shuntaro Mataka Kazufumi Takahashi Masashi Tashiro 《Journal of heterocyclic chemistry》1981,18(6):1073-1075
The reaction of 3,4-dibenzoyl-1-methyl-2,5-diphenylpyrrole ( 1 ) and -1-phenylpyrazole ( 2 ) with methylamines ( 3a-c ) afforded pyrrolo[3,4-c]pyridine ( 4 ), and isomeric 2H-pyrazolo[3,4-c]pyridines ( 5a-c ) and [4,3-c]pyridines ( 6a-c ), respectively. 相似文献
4.
J. Quiroga B. Insuasty S. Cruz P. Hernandez A. Bolaos R. Moreno Angelina Hormaza Regina H. S. de Almeida 《Journal of heterocyclic chemistry》1998,35(2):333-338
Several new pyrazolo[3,4-b]pyridines were obtained from the reaction of 5-amino-1-aryl-3-methylpyrazoles 1 with β-dimemylaminopropiophenones 2 in pyridine. The structure elucidation of 4,5-dihydropyrazolo[3,4-b]pyridines 3 is based on nmr measurements and X-ray diffraction. The treatment of compounds 3 with N-bromosuccinimide led to the formation of pyrazolo[3,4-b]pyridines 4 . 相似文献
5.
Klenov M. S. Ratnikov M. O. Churakov A. M. Solkan V. N. Strelenko Yu. A. Tartakovsky V. A. 《Russian Chemical Bulletin》2011,60(3):536-547
Methods for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides, which include the reaction of 3-nitramino-4-(R-phenyl)furazans or their O-methyl derivatives with electrophilic agents, have been developed. Unsubstituted [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide was synthesized from 3-nitramino-4-phenylfurazan upon the action of phosphorus anhydride or oleum, as well
as from O-methyl derivative of 3-nitramino-4-phenylfurazan upon the action of H2SO4, MeSO3H, CF3CO2H and BF3·Et2O, while 6-, 7-, 8-, and 9-nitro-substituted [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides — from the corresponding 3-nitramino-4-(nitrophenyl)furazans upon the action of the H2SO4-HNO3 nitrating mixture. A suggestion has been made that an oxodiazonium ion is formed in these reactions from nitramines or their
O-methyl derivatives upon the action of electrophilic agents, which is further involved into the intra-molecular reaction of
electrophilic aromatic substitution (S
EAr) with the aryl group. The structure of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-N-oxides was confirmed by 1H, 13C, and 14N NMR spectra. Theoretical studies by the B3LYP/6-311G(d,p) method of combined molecular system (O-methylated 3-nitramino-4-phenylfurazan + [H3SO4]+) resulted in calculation of thermodynamic parameters of the sequence of cascade elementary reactions leading to the formation
of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide. 相似文献
6.
E. G. Paronikyan S. N. Sirakanyan A. S. Noravyan 《Chemistry of Heterocyclic Compounds》1997,33(9):1101-1103
Tetrazolo[1,5-a]- and oxazolo[4,5-b]pyrano(thiopyrano)[3,4-c]pyridines, which are new heterocyclic systems, have been synthesized from pyrano[3,4-c]pyridine derivatives.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Armenian Academy of Sciences, Yerevan 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1260–1262, September, 1997. 相似文献
7.
E. S. Komarova V. A. Makarov L. M. Alekseeva G. V. Avramenko V. G. Granik 《Russian Chemical Bulletin》2007,56(11):2337-2343
Starting from the substituted 4,5-diaminopyrazolo[3,4-b]pyridine, derivatives of a number of tricyclic systems, viz., imidazo[4,5-d]pyrazolo[3,4-b]pyridine, pyrazolo[3,4-b][1,2,5]thiadiazolo[3,4-d]pyridine, pyrazolo[3,4-b][1,2,3]triazolo[4,5-d]pyridine, and [1,3]oxazolo[5,4-b]pyrazolo[4,3-e]pyridine, were synthesized and reaction schemes for the processes were proposed. 相似文献
8.
Diethoxymethyl acetate was used to cyclize o-disubstituted aminopyridines to oxazolo[4,5-c]pyridines and imidazo[4,5-c]pyridines. All the possible imidazole-methylated imidazo[4,5-c]pyridines were prepared. A novel synthesis of 2-substituted thiazolo[5,4-c]pyridines and 4-amino-3-pyridinethiol was discovered. 相似文献
9.
Salo Gronowitz Curt Roos Elina Sandberg Sergio Clementi 《Journal of heterocyclic chemistry》1977,14(5):893-897
Deuteriodeprotonation of some substituted 4,5-borazarothieno[2,3-c]pyridines (I) and 7,6-borazarothieno[3,2-c]pyridines (II) has been studied by the nmr technique. Exchange occurred predominantly in the 3-position, and the effect of methyl substitution on rate is discussed. The rates of exchange in some derivatives of I and II were compared with those of the isoelectronic thieno[2,3-c]pyridines (III) and thieno[3,2-c]pyridines (IV). Similar rates were obtained, confirming the aromatic nature of I and II. The deuteriodeprotonation of 4-methyl-4,5-borazaro-thieno[2,3-c]pyridine (Ie), 7-methyl-7,6-borazarothieno[3,2-c]pyridine (IIe), 4-methylthieno-[2,3-c]pyridine (IIIe), and 7-methylthieno[3,2-c]pyridine (IVe) were measured at different concentrations of deuteriosulfuric acid and different temperatures, showing that the protonated heterocycles are substrates in the deuteriodeprotonation reaction. Standard rates at p0 H and 100° were calculated for these systems. 相似文献
10.
The synthesis and characterization of a number of 3-aryl-6H-isoxazolo[3,4-d]pyrazolo[3,4-b]pyridines and 3-aryl-6H-isoxazolo[5,4-d]pyrazolo[3,4–6]pyridines from common precursors, 5-benzoyl-4-chloro-1H-pyrazolo-[3,4-b]pyridines, has been described. The structures were determined by unambiguous chemical synthesis and by isolation and 13C nmr analysis of some key, isolated, intermediates. The ability of these compounds to displace [3H]flunitrazepam from CNS binding sites was also observed. 相似文献
11.
Taisei Ueda Wataru Doi Shin‐Ichi Nagai Jinsaku Sakakibara 《Journal of heterocyclic chemistry》2000,37(5):1269-1272
Novel heterocycles [1,2,5]selenadiazolo[3,4‐e][1,4]diazepines 3a‐c , [1,2,5]thiadiazolo[3,4‐e]‐[1,4]diazepines 7a‐c , [1,2,5]selenadiazolo[3,4‐e][1,4]oxaepines 4a,b , [1,2,5]thiadiazolo[3,4‐e]‐[1,4]oxazepines 9a‐c and [1,2,5]selena(or thia)diazolo[3,4‐c][1,2,6]thiadiazines 10a,b were synthesized starting form 4,6‐dimethyl[1,2,5]se]enadiazolo[3,4‐d]pyrimidine‐5,7(4H,6H)‐dione 1 or 4,6‐dimethyl‐[1,2,5]thiadiazolo[3,4‐d]pyrimidine‐5,7(4H,6H)‐dione 5 . 相似文献
12.
Acetylacetone and malononitrile were coupled with diazotized arylamines to give arylazoacetyl-acetones and arylazomalononitriles.
When refluxed with 3-hydrazino-4,5-diphenyl-1H-pyrazolo-[3,4-c]pyridazine in the presence of ethanol/HCl, they yielded the corresponding 3-[4-(arylazo)-3,5-di-methylpyrazol-1-yl]- and
3-[3,5-diamino-4-(arylazo)pyrazol-1-yl]-4,5-diphenyl-1H-pyrazolo[3,4-c]pyri-dazine dyes. The dyes were applied to polyester and polyamide fabrics, and their spectral and fastness properties were
measured. 相似文献
13.
Jean-Louis Ripoll Yannick Valle Mohamed Khalid Abdelhak Hakiki 《Journal of heterocyclic chemistry》1992,29(7):1867-1868
4,5-Dihydro-1H,3H-thieno[3,4-c]thiophene and 4,5-dihydro-1H,3H-thieno[3,4-c]furan were synthesized by retro Diels-Alder reactions under flash vacuum thermolysis conditions. 相似文献
14.
S. N. Sirakanyan E. G. Paronikyan M. S. Ghukasyan A. S. Noravyan 《Chemistry of Heterocyclic Compounds》2010,46(6):736-741
A method for the synthesis of new 8-amine derivatives of pyrano[4",3":4',5']pyrido[3',2':4,5]furo-[3,2-d]pyrimidines based on 6-oxo derivatives of pyrano[3,4-c]pyridines has been developed. 相似文献
15.
New methods for the preparation of 3,4-diaminopyridine (5) and imidazo[4,5-c]pyridines 7a,7b based on direct nitration of 4-acylaminopyridines 3a, 3b have been explored. 相似文献
16.
L. M. Mironovich M. A. Ivanov E. P. Koval'chuk 《Chemistry of Heterocyclic Compounds》2001,37(9):1150-1152
8-tert-Butyl-9-oxo-1,2,4-triazolo[4,5-b]-1,2,4-triazolo[3,4-c]-1,2,4-triazine has been synthesized by the interaction of 6-tert-butyl-3-hydrazino-1,2,4-triazolo[3,4-c]-1,2,4-triazin-5-one with formic acid. The conditions of carrying out the reaction are discussed. Spectral characteristics are given. 相似文献
17.
L. V. Grishchuk E. I. Ivanov V. E. Kuz'min A. M. Turyanskaya R. Yu. Ivanova 《Chemistry of Heterocyclic Compounds》2003,39(3):340-343
The reaction of 4-aryl-2-hydrazino-3-nitro-6-R-quinolines with NaNO2 in AcOH gives the corresponding tetrazolo[1,5-a]quinolines. In contrast to tetrazolo[1,5-c]pyrimidines they cannot be converted to 6-R-4-phenyl[1,2,5]oxadiazolo[3,4-b]quinoline-3-oxides by heating in THF, toluene, or AcOH. Total energy quantum-chemical calculations using the MINDO/3 and MNDO methods show that [1,2,5]oxadiazolo[3,4-b]quinoline-3-oxides are significantly higher in energy (230-280 kcal/mol) than the mentioned tetrazolo[1,5-a]quinolines and hence their formation is unlikely. 相似文献
18.
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
19.
Tze-Ming Chan R. Friary H. Jones J. H. Schwerdt V. Seidl A. S. Watnick S. M. Williams 《Journal of heterocyclic chemistry》1990,27(4):1135-1142
1-Phenylmethyl- and 1-(4-methoxyphenylmethyl)-5-chloro-1,2,3-triazole-4-carbonyl chlorides acylated the pyrrolidine enamines of cyclopentanone and cyclohexanone, and the resulting enaminones underwent transaminations with aryl amines under acidic conditions. The products then cyclized under basic conditions to linearly fused, tricyclic 3-phenylmethyl- and 3-(4-methoxyphenylmethyl)-4-aryl-8-oxo-4,5,6,7-tetrahydrocyclopenta[6]-1,2,3-triazolo[4,5-e]pyridines, and to 5,6,7,8-tetrahydro-4-aryl-3H-1,2,3-triazolo[4,5-b]quinolin-9(4H)-ones. Similar transaminations afforded the related 8-phenyl- and 8-(3-chlorophenyl)-1,5,7,8-tetrahydro-1-(phenylmethyl)-4H-thieno[3,4-e]-1,2,3-triazolo[4,5-b]pyridin-4-ones. Phase-transfer and catalytic hydrogenolyses of some of these intermediates furnished 4-aryl-8-oxo-4,5,6,7-tetrahydrocyclopenta[b]-1,2,3-triazolo[4,5-e]pyridines and 4-aryl-5,6,7,8-tetrahydro-3H,2,3-triazolo[4,5-b]quinoline-9-(4H)-ones. The 3-(4-methoxyphenylmethyl)-4-aryl intermediates were sterically crowded. Two protons from the methoxyphenylmethylphenylmethylgroups were dramatically shielded because of anisotropic effects exerted by the 4-aryl substituents. 相似文献
20.
Marino Artico Silvio Massa Giorgio Stefancich Romano Silvestri Roberto Di Santo Federico Corelli 《Journal of heterocyclic chemistry》1989,26(2):503-507
The preparation of 5-dimethylaminoethyl-4,6-dioxo-1-phenyl-1,4,5,6-tetrahydropyrazolo[3,4-e]pyrrolo-[3,4-g]indolizine, a derivative of the still unknown tetracyclic parent ring pyrazolo[3,4-e]pyrrolo[3,4-g]indolizine, is reported starting from 1-phenyl-5-(1-pyrryl)pyrazole-4-acetonitrile by PPA catalyzed double cyclization of the related oxalylcyanomethyl derivative and subsequent alkylation. The synthesis of 4,5-bis(isopro-pylaminocarbonyloxymethyl) and 4,5-bis-(cyclohexylaminocarbonyloxymethyl) derivatives of 1-phenyl-1H-pyrazolo[3,4-e]indolizine is also described. The new tricyclic and tetracyclic derivatives were tested as potential antitumor agents. 相似文献