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1.
Malononitrile reacted with the title compound to give 6-amino-5-cyano-2-(3,3-dicyano-2-methylallylidene-4-methyl-2H-pyran (3). Treatment of 3 with hot 80% sulfuric acid yielded 4,7-dimethyl-56-hydroxy-2(1H)quinolone. With concentrated aqueous sodium hydroxide, 3 gave 5-amino-3,6-dicyano-4,7-dimethyl-2(1H)quinolone and 5-amino-6-carbamoyl-3-cyano-4,7-dimethyl-2(1H)quinolone. The reaction of 3 with hydrochloric in acetic acid gave a mixture of 6-amino-3,7-dicyano-2,8-dimethyl-4-quinolizone and 3-cyano-4-methyl-6-(3,3-dicyano-2-methylallyl)-2-pyrone. Compound 3 also reacted with methylamine, butylamine and piperidine to give 8-amino-5-cyano-4-methyl-2-pyridone, 6-bulylamino-5-cyano-4-methyl-2-pyridone and 5-eyano-4-methyl-6-piperidino-2-pyridone respectively. 相似文献
2.
Alberto Bargagna Pietro Schenone Filippo Evangelisti 《Journal of heterocyclic chemistry》1979,16(1):93-96
The dipolar 1,4-cycloaddition of dichloroketene to N,N-disubstituted 3-amino-1-phenyl-2-propene-1-onesled directly to N,N-disubstituted 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones only in the case of an usual aliphatic N,N-disubstitution. In the case of partial or full aromatic N-substitution, N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-6-phenyl-2H-pyran-2-ones were instead obtained, which were dehydrochlorinated with DBN to the corresponding 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones. 相似文献
3.
Takeshi Aoyagi Reiko Yanada Kiyoshi Bessho Fumio Yoneda W. L. F. Armarego 《Journal of heterocyclic chemistry》1991,28(6):1537-1539
10-Alkyl-2-amino-2-deoxo-5-deazaflavins were prepared by the condensation of 2-amino-6-chloro-5-formylpyrimidin-4(3H)-one with the corresponding N-alkylanilines. 2-Amino-10-p-tolyl-2-deoxo-5-deazaflavin was prepared by the condensation of 2-amino-6-p-toluidinopyrimidin-4(3H)-one with o-chlorobenzaldehyde. Some reactivities of 2-aminopyrimidin-4(3H)-ones are described. 相似文献
4.
Harry L. Yale 《Journal of heterocyclic chemistry》1977,14(2):207-208
The annulation of 2-amino-3-hydroxy-, 2-amino-3-carboxy-, and 2-amino-3-methylpyridine with ethyl cyelopenlanone-2-earboxylate led to the 5-hydroxy-, 2 , 5-carboxy-, 3, and 5-methyl-, 4 , derivatives of the 2,3-dihydrocycloperita[d]pyrido[1,2-a]pyrimidin-10(1H) one heterocycle. Alkylation of 2 with α-bromotolue, ne gave the 5-benzyloxy derivative. 相似文献
5.
The preparation of isonipecotinoyl analogues of aminopterin and methotrexate is described. Condensation of diethyl N-isonipecotinoyl-L-glutamate 4 with 2-amino-5-bromomethyl-3-cyanopyrazine 5 afforded diethyl N-(N-[(2-amino-3-cyanopyrazin-5-yl)methyl]isonipecotinoyl)-L-glutamate 6 . Cyclisation of 6 with guanidine followed by blocking group hydrolysis afforded N-([N-(2,4-diaminopteridin-6-yl)methyl]isonipecotinoyl)-L-glutamic acid 8 . Coupling of N-(2-amino-4(3H)ioxopteridin-6-yl]methyl)isonipecotinic acid 11 with diethyl L-glutamate gave diethyl N-[(N-[2-amino-4(3H)-oxopteridin-6-yl]methyl)isonipecotinoyl]-L-glutamate 12 . Blocking group hydrolysis afforded N-[(N-[2-amino-4(3H)-oxopteridin-6-yl]methyl)isonipecotinoyl]-L-glutamic acid 13 . 相似文献
6.
Alberto Bargagna Sergio Cafaggi Pietro Schenone 《Journal of heterocyclic chemistry》1980,17(3):507-511
Cycloaddition of dichloroketene to N,N-disubstituted 1-amino-4-methyl-1-penten-3-ones and 1-amino-4,4-dimethyl-1-penten-3-ones occurred in moderate to fair yield only in the case of aromatic N-substitution to give N,N-disubstituted 6-alkyl-4-amino-3,3-dichloro-3,4-dihydro-2H-pyran-2-ones, which were dehydrochlorinated with DBN to afford in good yield N,N-disubstituted 6-alkyl-4-amino-3-chloro-2H-pyran-2-ones. In the case of aliphatic N,N-disubstitution, cyclo-addition led directly to 6-alkyl-4-dialkylamino-3-chloro-2H-pyran-2-ones only for N,N-disubstituted 1-amino-4,4-dimethyl-1-penten-3-ones. The reaction between 1-dimethylamino-4-methyl-1-penten-3-one and dichloroketene gave 3-chloro-4-dimethylamino-3,6-dihydro-6-isopropylidene-2H-pyran-2-one in low yield. 相似文献
7.
Hassan Attia Elfahham Fathy Mohamed Abdel-Galil Yusria Rizk Ibraheim Mohamed Hilmy Elnagdi 《Journal of heterocyclic chemistry》1983,20(3):667-670
Several new pyrazolo[1,5-a]pyrimidines and pyrano[2,3-c]pyrazoles were synthesized viathe reaction of the cinnamonitrile derivatives 1a-c with 5-amino-3-phenylpyrazole ( 1 ), 3-amino-2-pyrazolin-5-one ( 2 ) and 3-amino-1-phenyl-2-pyrazolin-5-one ( 22 ). 相似文献
8.
Barabanov I. I. Fedenok L. G. Polyakov N. E. Shvartsberg M. S. 《Russian Chemical Bulletin》2001,50(9):1663-1667
When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl)naphtho[2,3-g]indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho[2,3-h]quinoline-7,12-diones. Heating of the starting phenylpropynol with Et3N causes its dehydrogenation and isomerization. 相似文献
9.
3-Amino-1,1-dichloro-5/6-phenyl-1H-isoindole hydrochloride was reacted with 5-amino-2-imino-3,4-diphenyl-2H-pyrrole or 5-amino-2-imino-3,4-ethylenedithio-2H-pyrrole to obtain unsymmetrical phenyl-substituted porphyrazines. 相似文献
10.
Fernando De Andrés Mohammed Zougagh Gregorio Castañeda Angel Ríos 《Analytical and bioanalytical chemistry》2010,397(1):223-231
A rapid and simple method for separation and detection of six heterocyclic aromatic amines (2-amino-1-methyl-6-phenylimidazo
[4,5-b]-pyridine, 2-amino-1-methyl-imidazo [4,5-f]-quinoline, 2-amino-3,8-dimethyl-imidazo [4,5-f]-quinoxaline, 2-amino-3,7,8-trimethyl-imidazo [4,5-f]-quinoxaline, 2-amino-3,4,8-trimethyl-imidazo [4,5-f]-quinoxaline, and 2-amino-3,4-dimethyl-imidazo [4,5-f]-quinoline) in human urine samples is proposed to reflect daily intake and recent HAAs exposure. This method comprises previous
clean-up and preconcentration of the analytes on Strata-X reversed phase extraction cartridges followed by capillary liquid
chromatography (CLC) and evaporative light-scattering detection (ELSD). A mobile phase of acetonitrile and ammonium acetate
35 mM at pH 5.15 through a gradient of composition and a flow rate of 15 μL min−1 resulted in good separations of the analytes. Temperature and gas pressure were optimized for detection. The CLC-ELSD allows
the separation and quantification of HAAs with good resolution, precision, and sensitivity. The usefulness of the proposed
method was demonstrated by the analysis of synthetic and natural human urine samples spiked with different concentration levels
of heterocyclic amines. 相似文献
11.
Cyril Prknyi Hui Liang Yuan Nam Sook Cho Jin-Hwa J. Jaw Tamar E. Woodhouse Thomas L. Aung 《Journal of heterocyclic chemistry》1989,26(5):1331-1334
The synthesis of two new acyclic nucleoside analogs, 2-(2′,3′-dihydroxypropyl)-5-amino-2H-1,2,4-thiadiazol-3-one (1) and 3-(2′,3′-dihydroxypropyl)-5-amino-3H-1,3,4-thiadiazol-2-one (2), is reported. The first compound, 1, was obtained by reaction of 3-chloro-1,2-propanediol with the sodium salt of 5-amino-2H-1,2,4-thiadiazol-3-one (3) in anhydrous dimethylformamide. Similarly, 5-amino-3H-1,3,4-thiadiazol-2-one (4) reacted with 3-chloro-1,2-propanediol to give 2. The thiadiazole 4 was prepared by condensation-cyclization of hydrazothiodicarbonamide (9). 相似文献
12.
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
13.
The reaction of 2-amino-1,1-dicyanobut-1-ene and 2-amino-1,1-dicyano-2-phenylethene, respectively, with N,N-dimethylformamide dimethylacetal provided the corresponding (N,N-dimethylaminomethylene)amino derivatives. 2-[(N,N-Dimethylaminomethylene)amino]-1,1-dicyano-2-phenylethene was converted into 4-amino-5-cyano-6-phenylpyrimidines by treatment with primary aliphatic and aromatic amines. The structure of the reaction products was confirmed by 13C nmr spectroscopy. 相似文献
14.
An Ullmann reaction between 2-bromonicotinic acid and 2,6-diaminopyridine gave 6 -amino-2,2 -dipyridylamino-3-carboxylic acid (V). The latter was converted into 7-amino-5H-dipyrido-[1,2-a:2,3 -d]pyrimidin- 5-one (VII) by heating with polyphosphoric acid and into 2-amino-5,10 H-anthyridin-5-one (VIII) by heating with concentrated sulfuric acid. Structure proofs of VII and VIII are given and some derivatives of VIII are described. 相似文献
15.
L. M. Alekseeva T. I. Mukhanova E. K. Panisheva O. S. Anisimova K. F. Turchin A. V. Komkov V. A. Dorokhov V. G. Granik 《Russian Chemical Bulletin》1999,48(1):160-165
Nenitzescu reaction of acetyl ketene aminals (N,N-acetals) was investigated. The interaction of 2-acetyl-1-amino-1-anilinoethene with benzoquinone gave 3-acetyl-2-amino-7a-hydroxy-1-phenyl-5,7a-dihydro-1H-indol-5-one, which was then transformed into 3-acetyl-2-amino-6-chloro-5-hydroxy-1-phenylindole. The reaction of benzoquinone
with 2-acetyl-1-amino-1-benzoylaminoethene led to the corresponding hydroquinone-adduct which was oxidized to 4-acetylamino-5-(2,5-dihydroxyphenyl)-2-phenyloxazole.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 160–165, January, 1999. 相似文献
16.
Masaru Senuma Katsuhiko Nakamichi Koichi Nabe Shigeru Nishimoto Tetsuya Tosa 《Applied biochemistry and biotechnology》1989,22(2):141-150
An industrial production method of L-2-amino-4-phenylbutyric acid from 2-oxo-4-phenylbutyric acid by microbial cells containing
aminotransferase activity was investigated. By usingParacoccus denitrificans pFPr-1, 0.19M L-2-amino-4-phenylbutyric acid was produced with a 95% conversion yield. Accumulated L-2-amino-4-phenylbutyric acid was readily
isolated in pure form. Overall yield from 2-oxo-4-phenylbutyric acid was 83.7%. 相似文献
17.
Treatment of 2,3-dichloroquinoxalines with 2-amino-6-picoline-3-thiol gave a mixture of 2,3-bis(2-amino-6-picolinyl-3-thio)quinoxalines ( 16 , R = H, CI) and 2,3-bis (N,N-dimethylamino)quinoxalines ( 15 , R = H, CI) separated by fractional crystallization. A similar reaction of 3-amino-6-methoxypyridine-2(1H)-thione ( 9 ) with 4,5-dichloropyridazin-3(2H)-one ( 21 ) gave 4-chloro-5-(3-amino-6-methoxypyridyl-2-thio)pyridazin-3(2H)-one ( 22 ). Concentrated hydrochloric acid-catalysed cyclization of 22 gave the non-rearranged 7-methoxy-2,3,6-triazaphenothiazin-1(2H)-one. The action of compound 22 in refluxing glacial acetic acid gave, on the other hand, 7-methoxy-2,3,6-triazaphenothiazin-4(3H)-one via a Smiles rearrangement. These cyclized compounds are the first known derivatives of the new 2,3,6-triazaphenothiazine ring system. 相似文献
18.
Tret'yakova E. V. Flekhter O. B. Galin F. Z. Spirikhin L. V. Tolstikov G. A. 《Russian Journal of Organic Chemistry》2003,39(12):1738-1740
Condensation of cyclopentanonopimaric acid with malononitrile in the presence of p-methoxybenzaldehyde or elemental sulfur gave the corresponding fused 2-amino-3-cyano-4-(4-methoxyphenyl)-4H-pyrano and 2-amino-3-cyanothieno derivatives. 相似文献
19.
Alberto Bargagna Pietro Schenone Francesco Bondavalli Mario Longobardi 《Journal of heterocyclic chemistry》1982,19(2):257-261
Cycloaddition of dichloroketene to N,N-disubstituted (E)-amino-5-methyl-1,4-hexadien-3-ones IV and (E,E)-1-amino-5-phenyl-1,4-pentadien-3-ones V occurred in moderate to good yield only in the case of aromatic N-substitution to give N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-6-(2-methyl-l-propenyl) (2-phenylethenyl)-2H-pyran-2-ones, which were dehydrochlorinated with DBN to afford in good yield N,N-disubstituted 4-amino-3-chloro-6-(2-methyl-propenyl)(2-phenylethenyl)-2H-pyran-2-ones. In the case of aliphatic N,N-disubstitution (dimethylamino group) of enaminones IV and V, the Cycloaddition led directly in low yield to 3-chloro-4-dimethylamino-6-(2-methyl-l-propenyl)(2-phenylethenyl)-2H-pyran-2-ones. 相似文献
20.
Do Young Ra Nam Sook Cho Jung Hyun Moon Sung Kwon Kang 《Journal of heterocyclic chemistry》1998,35(6):1435-1439
5-Amino-2-acyl-1,2,4-thiadiazolin-3-ones 2–1 can be synthesized from 5-amino-2H-1,2,4-thiadiazolin-3-one ( 1–1 ) via a selective acylation with an acid anhydride in pyridine. The 1H nmr spectral characteristics of 5-amino-2-acyl-1,2,4-thiadiazolin-3-ones 2–1 is in particular, compared with 5-amino-2H-1,2,4-thiadiazolin-3-one ( 1–1 ) and 5-amino-2-alkyl-1,2,4-thiadiazolin-3-ones 1–2, 1–3 . The 5-amino group of 2–1 appeared as two peaks in its 1H nmr spectrum, which merged to a single peak at a higher temperature, while those of compound 1–1, 1–2 and 1–3 appear only as a single peak. The restricted rotation of the C(5)-N(5) (at amino) bond of 5-amino-2-acetyl-1,2,4-thiadiazolin-3-one (2a-1) is about 14.5 Kcal/mol. 相似文献