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1.
Tomoji Aotsuka Yoshihisa Okamoto Kaname Takagi Michel Hubert-Habart 《Journal of heterocyclic chemistry》1991,28(2):485-487
The ring contraction of 4-ammo-1H-1,5-benzodiazepine-3-carbonitrile hydrochloride 1 and ethyl 4-amino-1H-1,5-benzodiazepine-3-carboxylate hydrochloride 2 with aromatic primary amines into benzimidazole derivatives 3 and 4 was readily accomplished by heating in methanol. Benzodiazepine 1 also reacted with methylamine and ethylamine at about 40° to give ring-opened amine adducts 7 which were recyclized to 1 with hydrochloric acid. 相似文献
2.
Kaname Takagi Tomoji Aotsuka And Hikari Morita Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1986,23(5):1443-1449
Reactions of 4-ethoxycarbonylamino-1H-1,5-benzodiazepine-3-carbonitrile (2) with aliphatic primary amines gave 1-substituted 4-(2-aminoanilino)pyrimidin-2(1H)-one-5-carbonitriles 3. Analogous reactions of 2 with aromatic primary amines afforded 2-(2′-anilino-1′-cyanovinyl)benzimidazoles 5 and 6. Upon treatment with triethylamine, 3 underwent intramolecular cyclization to give 3-substituted 5-aminopyrimidino[4,5-b]-[1,5]benzodiazepin-2(3H,11H)-ones 8 . Heating of 3 with p-toluenesulfonic acid in ethanol gave 2-substituted pyrimidino[1,6-a]benzimidazol-1(2H)one-4-carbonitriles 9 . Reactions of 2 with hydrazines were also described. Mechanistic pathways are proposed to account for the products. 相似文献
3.
Two seven-membered ring compounds and three five-membered ring compounds were obtained by reaction in hot xylene of 3,3-dimercapto-l-phenyl-2-propen-1-one (1) with N-alkyl-o-phenylenediamines (2) . Compounds isolated were the 4-phenyl-5-alkyl-1,5-dihydro-2H-1,5-benzodiazepine-2-thiones (3) the 1-alkyl-4-phenyl-1,3-dihydro-2H-1,5-benzodiazepine-2-thiones (4) , the 1-alkyl-2-phenacylbenzimidazoles (5) , the 1-alkyl-2-phenylbenzimidazoles (6) and the 1-alkyl-2-methylbenzimidazoles (7) . The structures of these compounds were elucidated from their chemical reactivity and their nmr and ir spectra. 相似文献
4.
Yoshihisa Okamoto Isao Togo Yoshihisa Kurasawa Kaname Takagi 《Journal of heterocyclic chemistry》1986,23(6):1829-1831
The reactions of multifunctional compounds 2a, b, c, 3a, b and 4a, b which were readily obtained from 4-amino-1H-1,5-benzodiazepine-3-carbonitrile 1 with orthoesters are described, and derivatives of pyrazolo-[3,4-d]pyrimidines 5 , pyrimido[1,6-a]benzimidazole 9 , and pyrazolo[3′,4′:4,5]pyrimido[1,6-a]benzimidazole 10 are synthesized. 相似文献
5.
R. Pennini A. Cerri A. Tajana D. Nardi F. Giordano 《Journal of heterocyclic chemistry》1988,25(1):305-310
Reaction of 4-chloro-1,2-benzenediamine with 3,3-dimercapto-1-phenyl-2-propen-1-one afforded, as expected, a mixture of 7-chloro and 8-chloro-1,3-dihydro-4-phenyl-2H-1,5-benzodiazepine-2-thione. After separation of the two components and further reaction, their structure was established by chemical degradation of 7-chloro-2-(2-diethylaminoethylthio)-4-phenyl-3H-1,5-benzodiazepine to 5-chloro-1,3-dihydro-1-methyl-2H-benzimidazol-2-one. The structure was also confirmed by single X-ray analysis of 7-chloro-2-(2-diethylaminoethylthio)-4-phenyl-3H-1,5-benzodiazepine. 相似文献
6.
The reaction of 2H-thiopyran-3,5(4H,6H)-dione with N,N-dimethylformamide dimethyl acetal gave in good yield 4-dimethylaminomethylene-2H-thiopyran-3,5(4H,6H)dione (II), which afforded 1-substituted 5,7-dihydrothiopyrano[3,4-c]pyrazol-4(1H)-ones with aliphatic and aromatic hydrazines, 5H-thiopyrano[4,3-d]isoxazol-4(7H)-one (IV) with hydroxylamine hydrochloride and 2-substituted 6H-thiopyrano[3,4-d]pyrimidin-5(8H)-ones with amidines and guanidines, generally in satisfactory yields. 4-(t-Butylhydrazonoformyl)-2H-thiopyran-3,5(4H,6H)-dione was isolated as an intermediate in the reaction of II with t-butylhydrazine, whereas formamidine gave with II 4-iminoformyl-2H-thiopyran-3,5(4H,6H)-dione as the sole product. The isoxazole IV isomerized easily with sodium methoxide to 3,4,5,6-tetrahydro-5,5-dihydroxy-3-oxo-2H-thiopyrano-4-carbonitrile. 相似文献
7.
The reaction of 5a-acetyl-6-ethoxycarbonyl-5a,6a-dihydro-6H-cyclopropa[e]pyrazolo[1,5-a]pyrimidine-3-carbonitrile ( 1a ) with benzylamine gave ethyl l-benzyl-5-cyano-8a,9-dihydro-2-methyl-1H-pyrrolo[3,4-e]-pyrazolo[1,5-a]pyrimidine-8a-carboxylate ( 2a ), in addition to 5-acetyl-3-benzylamino-1-(4-cyanopyrazol-3-yl)- 2-pyridone ( 3 ). Reaction of 1a with aniline gave ethyl 6-acetyl-8-anilino-3-cyano-7,8-dihydro-4H-pyrazolo-[1,5-a][1,3]diazepine-8-carboxylate ( 4 ), in addition to ethyl 3-cyano-7-methyl-6-pyrazolo[1,5-a]pyrimidine-acrylate ( 5 ). On the other hand, the same reactions of 1b with benzylamine or aniline gave 2b or 8b , respectively. Though catalytic hydrogenation of 1a over 5% palladium-carbon proceeded by ring fission of cyclopropane ring to give 9 , 1a (or 1b ) afforded 4,5-dihydro derivatives ( 13 or 15 ) by catalytic hydrogenation over platinum oxide. The reactivity of 5-methoxy-4,5,5a,6a-tetrahydro-6H-cyclopropa[e]pyrazolo[1,5-a]pyrimidine ( 16 ), which are related analogs of 1a,b , is also described. 相似文献
8.
Synthetic routes leading to the preparation of 4-substituted 1,4-benzodiazepine-3,5-diones are described. Thus, 2-carbobenzoxyaminobenzoic acid was converted to its p-nitrobenzyl ester (I) and the decarbobenzoxylated product (II) gave, with ethyl α-bromoacetate, N-(2-carboxy p-nitrobenzylate)phenylglycine ethyl ester (III). The latter was hydrogenolyzed to N-(2-car-boxy)phenylglycine ethyl ester (IV), which was coupled with benzylamine to give N-(2-carboxy-benzylamido)phenylglycine ethyl ester (VIa). Saponification of VIa afforded N-(2-carboxy-benzylamido)phenylglycine (VIIa) which was cyclized with DCCI to produce 4-benzyl-2H-1,4-benzodiazepine-3,5(lH,4H)dione (VIIIa). Alternatively, 2-nitro-N-phenylbenzamide (Xb) was reduced to 2-amino-N-phenylbenzamide (XIb) which was converted to N-(2-carboxanih'do)-phenylglycine ethyl ester (VIb). The latter was converted to 4-phenyl-2H-1,4-benzodiazepine-3,5(1H,4H)dione (VIIIb) in an analogous fashion described for VIIIa. 相似文献
9.
Kurdina L. N. Zalesov V. V. Kozlov A. P. 《Russian Journal of Organic Chemistry》2002,38(10):1534-1537
4,N-Diaryl-1,5-benzodiazepine-2-carboxamides were synthesized by acid-catalyzed reaction of (Z)-4,N-diaryl-2-hydroxy-4-oxo-2-butenamides with o-phenylenediamine or N,N'-bis(triphenylphosphoranediyl)-o-phenylenediamine. The reaction mechanism is discussed. 相似文献
10.
Pteridine derivatives related to folic acid and methanopterin were synthesized by two methods. The first synthesis is initiated by the radical substitution of 5-methylpyrazine-2,3-dicarbonitrile (3) with the (N-acylanilino)alkyl radical to give 6-methyl-5-(N-acylanilino)alkylpyrazine-2,3-dicarbonitrile (9) and was followed by the substitution of the 2-carbonitrile with methylamine and further conversion to 1-methyl-2-amino-6-(N-acylanilino)-alkyl-7-methylpteridin-4(1H)-imine 11 by the action of guanidine. The second method is initiated by radical hydroxymethylation of 5-methylpyrazine-2,3-dicarbonitrile (3) to give 5-hydroxy-methyl-6-methylpyrazine-2,3-dicarbonitrile (15), followed by oxidation of the hydroxymethyl group, N-phenylimination, and the substitution of the 2-carbonitrile with methylamine to give 6-methyl-2-methyl-arnino-5-(N-phenylimino)methenylpyrazine-3-carbonitrile (18). The reduction of the imino group and the final cyclization with guanidine gives 2-amino-6-anilinomethyl-1,7-dimethylpteridin-4(1H)-imine (20). 相似文献
11.
A series of new 4-aryl-1,3-dihydro-2H-1,5-benzodiazepine-2-thiones ( 3 ) has been synthesized by condensing the 3,3-dimercapto-1-aryl-2-propen-1-ones with o-phenylenediamine. The structure was established by the results of acid cleavage and by nmr spectra. The alkylation of compounds 3 gave 2-alkylthio-4-aryl-3H-1,5 benzodiazepines ( 10 ). 相似文献
12.
The syntheses of 2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides and 1,1-dioxides is described. The reaction of 1-carbamoyl-2-methylisothioureas 2 with thionyl chloride gave 2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides 3 in high yields. The treatment of 3 with either diazomethane or O-(2,4-dinitrophenyl)hydroxylamine furnished regioselectively N4-methylated and N4-aminated 2H-1,2,4,6-thiatriazin-3(4H)-one 1-oxides, respectively. Subsequent dimethylamination of 4 followed by oxidation with m-chloroperoxybenzoic acid led to 2H-1,2,4,6-thiatriazin-3(4H)-one 1,1-dioxides 6a-c . 相似文献
13.
The reaction of 4-chloro-2-phenyl-5-pyrimidinecarbonitrile (III) with N-methylglycinonitrile gave 4-[(eyanomethyl)methylamino]-2-phenyl-5-pyrimidinecarbonitrile (VIa), which upon cycli-zation under Dieckmann conditions afforded 5-amino-7-methyl-2-phenyl-7H-pyrrolo[2,3-d]-pyrimidine-6-carbonitrile (VIIa). Other examples (VIIb and VIIc) were prepared similarly from the reactions of III with glycinamide and ethyl glycinate, respectively. The preparation of simple 5-amino derivatives of the pyrrolo[2,3-d] pyrimidines thus synthesized is described. The alkyla-tion of VIIc with N-cyeloheptylchloroacetamide took place at the ring nitrogen, giving XII. The reaction of VIIa with formamide gave 4-amino-5-methyl-7-phenyl-5H-pyrrolo[2,3-d:4,5-d′ ]-dipyrimidine (XIII), the first member of a new ring system. Treatment of VIIa with carbon disulfide and pyridine afforded another example of this new ring system, 1,5-dihydro-5-methyl-7-phenyl-2H-pyrrolo[2,3-d:4,5-d′] dipyrimidine-2,4-(3H)dithione (XIV). 相似文献
14.
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
15.
8-Chloro-7-formyl-4-oxo-2-phenyl-4H-pyrimido[1,2-a]pyrimidine-3-carbonitrile ( 3 ) is constructed using N-(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl) acetamide ( 2 ) via Vilsmeier-Haack formylation reaction. Compound 3 reacted with 3-(triethoxysilyl)propan-1-amine under different conditions. Condensation of pyrimidopyrimidine 3 with thiosemicarbazone derivative gave Schiff base 8 , which upon treating with Vilsmeier-Haack reagent afforded pyrazole carbothioamide 9 . Cyclocondensation of compound 3 with some binucleophiles namely thiocarbohyrazide, hydrazine carbodithioic acid, benzyl hydrazinecarbodithioate and/or 2-thioxopyrimidinone was investigated. Structures of the new synthesized compounds were confirmed by their analytical and spectral data. 相似文献
16.
Eduardo Corts Corts María I. Becerra Lpez Yazmín M. Osornio Pichardo 《Journal of heterocyclic chemistry》1997,34(6):1833-1836
A series of twelve new 2-methylthio-3H-4-(p-substituted phenyl)-7-[(o-, and p-substituted)phenylthio]-1,5-benzodiazepines, which have potentially useful pharmacological properties, has been synthesized by condensing the 3,3-dimercapto-1-(para-substituted-phenyl)-2-propen-1-one with 3,4-diamino phenyl-R-phenylthio ethers, and subsequently the 1H-1,5-benzodiazepine-2-thiones obtained were treated with sodium hydride and methyl iodide. The structure of all products was corroborated by ir, 1H-nmr, 13C-nmr and ms. 相似文献
17.
The reaction of 3,4,4-trichloro-1-(2-thienyl)but-3-en-1-one with hydroxylamine gave 3-hydroxyiminomethyl-5-(2-thienyl)isoxazole
which was converted into 5-(2-thienyl)isoxazole-3-carbonitrile by the action of acetic anhydride in pyridine. 5-(2-Thienyl)isoxazole-3-carbonitrile
reacted with hydroxylamine to produce the corresponding amide oxime. Heterocyclization of its O-acyl derivatives in acetic acid afforded 5-substituted 3-[5-(2-thienyl)isoxazol-3-yl]-1,2,4-oxadiazoles. 相似文献
18.
The cyclization of aryl ketone anilides 3 with diethyl malonate to affords 4‐hydroxy‐6‐phenyl‐6H‐pyrano[3,2‐c]‐pyridin‐2,5‐diones 4 in good yields. 3‐Acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 5 are obtained by ring‐opening reaction of 4‐hydroxy‐6‐phenyl‐6H‐pyrano[3,2‐c]‐pyridin‐2,5‐diones 4 in the presence of 1,2‐diethylene glycol. The reaction of 3‐acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 5 with hydroxylamine hydrochloride produces 4‐hydroxy‐3‐[N‐hydroxyethanimidoyl]‐1‐phenylpyridin‐2(1H)‐ones 6 from which 3‐alkyloxyiminoacetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 7 are obtained by reacting with alkyl bromides or iodides in the presence of anhydrous potassium carbonate with moderate yields. The similar compounds can be synthesized on refluxing 3‐acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 5 with substituted hydroxylamine hydrochloride in the presence of sodium bicarbonate with good yields. Most of the synthesized compounds are characterized by IR and NMR spectroscopic methods. 相似文献
19.
A new and convenient procedure for the synthesis of 1,6-naphthyridin-2(1H)-ones and their derivatives is described. In the first scheme 5-acetyl-6-[2-(dimethylamino)ethenyl]-1,2-dihydro-2-oxo-3-pyridinecarbonitrile ( 4 ) obtained by the reaction of N,N-dimethylformamide dimethyl acetal with 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile ( 3 ) was cyclized to 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile ( 5 ) by the action of ammonium acetate. Thermal decarboxylation of acid 7 obtained from the hydrolysis of nitrile 5 led to a mixture of 5-methyl-1,6-naphthyridin-2(1H)-one ( 8 ) and its dimer 9 . Hydrazide 11 obtained from nitrile 5 in two steps was converted to 3-amino-5-methyl-1,6-naphthyridin-2(1H)-one ( 12 ) by the Curtius rearrangement. The amino group of 12 was readily replaced by treatment with aqueous sodium hydroxide to yield 3-hydroxy-5-methyl-1,6-naphthyridin-2(1H)-one ( 13 ). In the second scheme, Michael reaction of enamines of type 20 with methyl propiolate, followed by ring closure gave 5-acyl(aroyl)-6-methyl-2(1H)-pyridinones ( 21 ) which in turn were treated with Bredereck's reagent to produce 5-acyl(aroyl)-6-[2-(dimethylamino)ethenyl]-2(1H)-pyridinones ( 22 ). Treatment of 22 with ammonium acetate led to the formation of 1,6-naphthyridin-2(1H)-ones 23 . 相似文献
20.
Yasunori Sudoh Zhong-Tian Jin Kimiaki Imafuku Hisashi Matsumura 《Journal of heterocyclic chemistry》1982,19(3):525-528
The reaction of 3-acetyltropolone ( 1 ) with hydroxylamine under the acidic condition gave 3-methyl-8H-cyclohept[d]isoxazol-8-one ( 4 ) and its oxime ( 5 ), and under the neutral condition gave 4 and 3-acetyltropolone oxime ( 6 ). The reaction of 3-acetyl-2-methoxytropone ( 2a ) with hydroxylamine under the acidic condition gave 4, 5 , and 4-methyl-1H-2,3-benzoxazin-1-one ( 7 ), and under the neutral condition gave 4, 7 , 3-methyl-8H-cyclohept[c]isoxazol-8-one ( 8 ), and its oxime ( 9 ). The reaction of 7-acetyl-2-methoxytropone ( 2b ) with hydroxylamine under the acidic condition gave 4 and 5 , and under the neutral condition gave 5, 7 , and 9 . 相似文献