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271.
Summary The synthesis of some 5-cyano-4-hydroxy-2-pyridone derivatives (3 a–c) by condensation of 3-aminocrotononitrile (1) with substituted diethylmalonates (2 a–c) is described. Reaction of3 a with phosphorus oxychloride yields 4,6-dichloro-3-pyridinecarbonitrile (7 a), which reacts with various nucleophiles to give substituted 3-pyridinecarbonitriles (8–10).See ref. [1] 相似文献
272.
Thomas Kappe 《Journal of inclusion phenomena and macrocyclic chemistry》1994,19(1-4):3-15
The history of calixarene chemistry from the mid-thirties until 1978 is described.This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes. 相似文献
273.
Zusammenfassung o-Aminophenylglyoxal-dimethylacetal (1) läßt sich mit Carbonylverbindungen, die eine -Methylengruppe enthalten, im Sinne einerFriedländer-Synthese zu Derivaten des Chinolin-4-aldehyds umsetzen. Bei 150–160° reagiert1 mit Acetessigester und Malonester unter Bildung des 3-Acetyl-(11) bzw. 3-Car-bäthoxy-4-dimethoxymethyl-carbostyrils (12). o-Acetaminophenylglyoxal-dimethylacetal (21) kann mit Na-Äthylat zum Carbostyril-4-aldehyd-dimethylacetal (22) cyclisiert werden; mit Cyanessigester kondensiert sich21 zum 3-Cyan-4-dimethoxy-methyl-carbostyril (24).
Mit 1 Abbildung 相似文献
o-Aminophenylglyoxal-dimethylacetal (1) has been condensed with several cyclic ketones, acetophenones, and with acetone to yield derivatives of quinoline-4-aldehyde.1 reacts with ethyl acetoacetate and diethyl malonate at 160° yielding 3-acetyl-(11) and 3-carbethoxy-4-dimethoxymethyl-carbostyril (12) respectively. o-Acetaminophenylglyoxal dimethyl acetal (21) undergoes ring closure to carbostyril-4-aldehyde dimethyl acetal (22), when treated with sodium ethoxide; the reaction of21 with ethyl cyanoacetate leads to 3-cyano-4-dimethoxymethyl-carbostyril (24).
Mit 1 Abbildung 相似文献
274.
Zusammenfassung Salicylsäurechlorid (1) reagiert mit aromatischen Thioamiden unter HCl- und H2S-Abspaltung zu 4H-1,3-Benzoxazinonen (2–5), welche mit verd. HCl zu N-Acylsalicylsäureamiden (6–9) gespalten werden.
Salicyloyl chloride (1) reacts with aromatic thioamides to 4H-1.3-benzoxazinones (2–5), which can be hydrolized with dil. HCl yielding N-acyl-salicyloyl-amides (6–9).相似文献
275.
Zusammenfassung 3-Amino-4-hydroxycumarin (4), welches durch katalyt. Reduktion von 3-Phenylazo-4-hydroxycumarin (1) in 92proz. Ausb. zugänglich ist, wird beim Erhitzen mit 2n-NaOH in 3,6-Bis-(2-hydroxyphenyl)-2,5-dihydropyrazin (10) übergeführt. Die Dehydrierung von10 mit Pd liefert das entsprechende Pyrazin14, das auch aus dem o-Hydroxyphenylglyoxal-phenylhydrazon (13) gewonnen werden kann. Die Reduktion von10 mit Na/Butanol führt zum Piperazin18, die Reaktion mit Ac2O zum 1,4-Dihydropyrazinderivat17.
Mit 1 Abbildung 相似文献
3-Amino-4-hydroxycoumarin (4), obtained in 92% yield by the catalytic hydrogenation of 3-phenylazo-4-hydroxycoumarin (1), is readily converted by refluxing in 2N-NaOH to 3,6-bis-(2-hydroxyphenyl)-2.5-dihydropyrazine (10). The dehydrogenation of10 with a Pd catalyst yields the corresponding pyrazine14, which can also be obtained from the o-hydroxyphenylglyoxal-phenylhydrazone (13). The reduction of10 with sodium in butanol yields the known 2.5-bis(2-hydroxyphenyl)-piperazine (18); the reaction of10 with acetic anhydride leads by isomerization to the 1,4-diacetyl-3,6-bis(2-acetoxyphenyl)-1.4-dihydropyrazine (17).
Mit 1 Abbildung 相似文献
276.
A new synthesis of the indole system has been achieved by chclodehydrogenation of amino phenylmalonate heterocycles. Thus, the 4-amino coumarins1 a,b or the 4-amino-2-quinolones1 c–g are converted to the indoles2 with palladium on charcoal in boiling diphenyl ether. The reaction of the aminocompounds1 with diphenyl carbonate yields the fused polycyclic isoquinolones4. 相似文献
277.
Pérez R Beryozkina T Zbruyev OI Haas W Kappe CO 《Journal of combinatorial chemistry》2002,4(5):501-510
Solid-phase and solution-phase protocols for the synthesis of furo[3,4-d]pyrimidines, pyrrolo[3,4-d]pyrimidines, and pyrimido[4,5-d]pyridazines are reported. The multistep solid-phase sequence involves the initial high-speed, microwave-promoted acetoacetylation of hydroxymethylpolystyrene resin with methyl 4-chloroacetoacetate. The immobilized 4-chloroacetoacetate precursor was subsequently subjected to three-component Biginelli-type condensations employing urea and a variety of aromatic aldehydes. The resulting 6-chloromethyl-functionalized resin-bound dihydropyrimidones served as common chemical platforms for the generation of the desired heterobicyclic scaffolds using three different traceless cyclative cleavage strategies. The corresponding furo[3,4-d]pyrimidines were obtained by microwave flash heating in a rapid, thermally triggered, cyclative release. Treatment of the chloromethyl dihydropyrimidone intermediates with a variety of primary amines followed by high-temperature microwave heating furnished the anticipated pyrrolo[3,4-d]pyrimidine scaffolds via nucleophilic cyclative cleavage. In a similar way, reaction with monosubstituted hydrazines resulted in the formation of pyrimido[4,5-d]pyridazines. All compounds were obtained in moderate to good overall yields and purities. 相似文献
278.
[reaction: see text] Biologically active 4-aryl-3-alkenyl-substituted quinolin-2(1H)-ones have been synthesized in a short and concise manner employing readily available 4-hydroxyquinolin-2(1H)-ones as intermediates. Key steps in the synthesis include the derivatization of the quinolin-2(1H)-one cores using palladium-catalyzed Suzuki and Heck reactions, installing the 4-aryl and 3-alkenyl substituents. All synthetic transformations (six steps) required for the synthesis of the desired target quinolin-2(1H)-one were carried out using controlled microwave-assisted organic synthesis. 相似文献
279.
Thomas Kappe 《Monatshefte für Chemie / Chemical Monthly》1967,98(3):874-886
Zusammenfassung An der Methylgruppe substituierte -Picoline, insbesondere 2-Pyridylessigsäurederivate, reagieren mit unsubstit. oder monosubstit. Malonsäure-bis-trichlorphenylestern, Malonsäurechloriden oder Kohlensuboxid zu 2-Hydroxychinolizinonen-(4), die katalytisch zu 2-Hydroxy-6,7,8,9-tetrahydrochinolizinonen-(4) hydriert werden können.
Mit 2 Abbildungen.
Herrn Prof. Dr.F. Wessely zum 70. Geburtstag gewidmet. 相似文献
2-Alkylpyridines, especially derivatives of 2-pyridineacetic acid, react with unsubstituted and monosubstituted 2.4.6-trichlorophenyl malonates or malonyl chlorides or C3O2 to derivatives of 2-hydroxy-quinolizin-4-one. These compounds are hydrogenated in acetic acid in the presence of palladium to 2-hydroxy-6.7.8.9-tetrahydro-quinolizin-4-ones.
Mit 2 Abbildungen.
Herrn Prof. Dr.F. Wessely zum 70. Geburtstag gewidmet. 相似文献
280.
El-Sayed A. M. Badawey Samia M. Rida Farid S. G. Soliman Thomas Kappe 《Monatshefte für Chemie / Chemical Monthly》1989,120(1):73-76
Summary The synthesis of compound3 by condensing 1H-benzimidazole-2-acetonitrile (1) with ethyl cyclopentanone-2-carboxylate (2) in the presence of ammonium acetate is described. Methylation of3 with trimethyl phosphate yielded the N-methyl derivative4. Methods for converting3 to some of its related derivatives in which the carbonyl function was replaced by Cl, N3 and amines are also reported.
Kondensierte Ringsysteme des Benzimidazols, 3. Mitt.. Synthese von substituierten 2,3-Dihydrocyclopenta[4,5:2,3]pyrido[1,2-a]benzimidazol-11-carbonitrilen
Zusammenfassung Die Synthese der tetracyclischen Verbindung3 durch Kondensation von 1H-Benzimidazol-2-acetonitril (1) mit Cyclopentanon-2-carbonsäureester (2) in Gegenwart von Ammonacetat wird beschrieben. Die Methylierung von3 mit Trimethylphosphat liefert das N-Methylderivat4. Die Sauerstoffunktion in3 kann durch Chlor, Azid und Aminogruppen ersetzt werden.相似文献