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1.
Synthesis of exo- and endocyclic enamino derivatives of 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones
D. B. Rubinov I. L. Rubinova F. A. Lakhvich 《Russian Journal of Organic Chemistry》2011,47(3):319-330
Condensation of 2-acetylcyclohexane-1,3-diones with aromatic aldehydes in the presence of piperidine, pyrrolidine, hexamethyleneimine, or morpholine gave the corresponding 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones as the major products and 2-[3-aryl-1-cycloalkylaminoprop-2-en-1-ylidene]cyclohexane-1,3-diones as minor ones. Endocyclic enamino derivatives were synthesized in two steps through enol methyl ethers which reacted with amines. Endocyclic enamino derivatives of 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones containing an aryl group on the nitrogen atom readily underwent cyclization to 1,2,3,4,5,6,7,8-octahydroquinoline-4,5-dione derivatives. 相似文献
2.
D. B. Rubinov T. A. Zheldakova R. A. Zheldakova I. L. Rubinova A. V. Baranovski F. A. Lakhvich 《Russian Journal of General Chemistry》2012,82(1):122-130
Condensation of 2-propanoyl-, 2-butanoyl-, and 2-pentanoylcyclohexane-1,3-diones with aromatic aldehydes in the presence of
secondary amines (diethylamine, pyrrolidine, morpholine, piperidine, and hexamethyleneimine) leads to the formation of the
corresponding 2-[1-(dialkylamino)-2-alkyl-3-aryl-2-propylidene]cyclohexane-1,3-diones and derivatives of 4H-chromen-4,5(6H)-dione. A primary screening of some of the resulting enamino derivatives for fungicidal activity has been performed. 相似文献
3.
A. N. Pyrko 《Russian Journal of Organic Chemistry》2010,46(12):1843-1847
Three-component condensation of naphthalen-1-amine with triethyl orthoformate and dimedone or cyclopentane-1,3-dione, as well
as the reaction of naphthalen-1-amine with 2-acetyl-5,5-dimethylcyclohexane-1,3-dione, gave the corresponding 2-[1-(α-naphthylamino)alkylidene]cycloalkane-1,3-diones
which underwent intramolecular cyclization to 7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one derivatives on heating in polyphosphoric acid. 9,9-Dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one was reduced to 9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-ol with sodium tetrahydridoborate. 相似文献
4.
V. G. Kharchenko L. I. Markova Yu. T. Struchkov A. A. Espenbetov T. D. Kazarinova N. T. Komyagin 《Chemistry of Heterocyclic Compounds》1987,23(8):867-871
An x-ray crystallographic investigation of 7,7-dimethyl-2,3-di(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline, obtained by the hydrolysis of its oxime, was undertaken. The oxime, together with the isomeric oxime of 7,7-dimethyl-2,4-di(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline, is formed in the reaction of 5,5-dimethyl-2-[1,3-di(4-methoxyphenyl)-3-oxopropyl]cyclohexane-1,3-dione with hydroxylamine hydrochloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1085–1088, August, 1987. 相似文献
5.
O. V. Surikova A. G. Mikhailovskii N. N. Polygalova M. I. Vakhrin 《Russian Journal of Organic Chemistry》2008,44(6):845-848
Knoevenagel condensations of 5,5-dimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-diones with malononitrile, ethyl cyanoacetate, indan-1,3-dione, and Drotaverine base involved the ketone carbonyl group in the former with formation of deeply colored dark blue substances. The lactam ring in the products can be opened by the action of nitrogen-centered nucleophiles, e.g., p-toluidine. The reaction of 5,5-dimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-dione with methyl magnesium iodide gave 2-hydroxy-2,5,5-trimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinolin-3-one. 相似文献
6.
Malek T. Maghsoodlou Issa Yavari Farough Nassiri Hoorieh Djahaniani Zahra Razmjoo 《Monatshefte für Chemie / Chemical Monthly》2003,14(4):1585-1591
Alkyl isocyanides react with dialkyl acetylendicarboxylates in the presence of CH-acids such as cyclopentane-1,3-dione, cyclohexane-1,3-dione, or 5,5-dimethylcyclohexane-1,3-dione to afford highly functionalized 4H-pyrans in fairly high yields. In the case of reaction between dimethyl acetylenedicarboxylate and 5,5-dimethylcyclohexane-1,3-dione in the presence of cyclohexyl isocyanide or benzyl isocyanide tetrahydro-cyclopenta[b]pyran derivatives were isolated in addition to the 4H-pyran system. The free energy barrier (96.9kJmol–1) for restricted rotation around the polarized double bond of the enaminone moiety in dimethyl 2-[cyclohexylamino-(4,4-dimethyl-2,6-dioxocyclohexylidene)methyl]but-2-enedioate was determined by dynamic NMR spectroscopy. 相似文献
7.
Summary. Alkyl isocyanides react with dialkyl acetylendicarboxylates in the presence of CH-acids such as cyclopentane-1,3-dione, cyclohexane-1,3-dione, or 5,5-dimethylcyclohexane-1,3-dione to afford highly functionalized 4H-pyrans in fairly high yields. In the case of reaction between dimethyl acetylenedicarboxylate and 5,5-dimethylcyclohexane-1,3-dione in the presence of cyclohexyl isocyanide or benzyl isocyanide tetrahydro-cyclopenta[b]pyran derivatives were isolated in addition to the 4H-pyran system. The free energy barrier (96.9kJmol–1) for restricted rotation around the polarized double bond of the enaminone moiety in dimethyl 2-[cyclohexylamino-(4,4-dimethyl-2,6-dioxocyclohexylidene)methyl]but-2-enedioate was determined by dynamic NMR spectroscopy. 相似文献
8.
Active methylene compounds such as 5,5-dimethylcyclohexane-1,3-dione, cyclohexane-1,3-dione, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, 1,3-dimethyl-1H-pyrazol-5(4H)-one, and 3-methylisoxazol-5(4H)-one react with the 3-C position of N-confused porphyrin in THF for 5 min to afford a novel type of N-confused porphyrin derivatives in good yield without the need of any catalyst. 相似文献
9.
Jia-Yan Liu Jin-Xing Xu Xiao-Ming Qiao Ya Cai Dong-Sheng Chen 《Journal of heterocyclic chemistry》2020,57(11):3890-3897
A new series of pyrazino[2,3-a]acridine derivatives were prepared, via three-component reaction of quinoxalin-6-amine, aromatic aldehydes and 5,5-dimethyl cyclohexane-1,3-dione or cyclohexane-1,3-dione in ethanol as a solvent at reflux. The advantages of this protocol include mild reaction conditions, easy purification, high yields, and catalyst-free approach. 相似文献
10.
D. B. Rubinov T. A. Zheldakova I. L. Rubinova F. A. Lakhvich 《Russian Journal of Organic Chemistry》2008,44(7):1024-1030
2-(1-Alkoxyiminoalkyl)cyclohexane-1,3-diones undergo at heating Beckmann rearrangement to give 6,7-dihydro-1,3-benzoxazol-4(5H)-one derivatives that under treatment with amines in acid medium are converted into 1,5,6,7-tetrahydro-4H-benzimidazol-4-ones. In reaction of 6,7-dihydro-1,3-benzoxazol-4(5H)-ones with O-ethylhydroxylamine 4-ethoxyimino derivatives were obtained that treated with hydrochloric acid formed the corresponding N-ethoxybenzimidazolones. 相似文献
11.
Voronkova V. A. Komkov A. V. Shashkov A. S. Dorokhov V. A. 《Russian Chemical Bulletin》2011,60(1):148-152
The debenzoylation of 2-[(amino)(benzoylamino)methylidene]cyclohexane-1,3-diones (addition products of cyclohexane-1,3-diones
with benzoylcyanamide) affords the corresponding 2-diaminomethylidenecyclohexane-1,3-diones. The latter act as N,N-dinucleophiles in reactions with diethyl malonate in the presence of MeONa to form 6-hydroxy-2-(2,6-dioxocyclohexylidene)-1,2-dihydropyrimidin-4(3H)-ones. This reaction performed at 200 °C in the absence of bases results in the subsequent self-condensation of the dihydropyrimidinones
to give 4,5′-bipyrimidine derivatives. 相似文献
12.
在无溶剂条件下, 芳香醛与 5,5-二甲基-1,3-环己二酮或1,3-环己二酮经氨基磺酸锂催化缩合反应合成了氧杂蒽. 结果表明, 当催化剂用量为3%(摩尔分数)时, 在120 ℃反应 40~70 min, 产率高达 90% 以上. 此外, 探讨了该反应的氨基磺酸锂催化机理. 该合成方法具有操作简单, 反应时间短、 产率高及对环境友好等优点, 是现有氧杂蒽化合物合成方法的一个重要补充. 相似文献
13.
V. M. Berestovitskaya M. V. Selivanova M. I. Vakulenko I. E. Efremova G. A. Berkova 《Russian Journal of Organic Chemistry》2009,45(12):1814-1817
2-Benzylidene-3-methyl-4-nitro-2,5-dihydrothiophene 1,1-dioxide reacted with acyclic CH acids (acetylacetone, diethyl malonate,
and its derivatives) according to the 1,4-addition pattern, whereas reactions of the title compound with cyclohexane-1,3-dione
and 5,5-dimethylcyclohexane-1,3-dione (dimedone) were complicated by subsequent intramolecular heterocyclization leading to
thieno[3,2-b]chromene derivatives. 相似文献
14.
A new synthetic pathway to spiro[cyclohexane-1,3′-indoline]-2′,4-diones was found starting from 3-chloromethylene-2-indolones 1 and Danishefsky's diene 2. Their synthesis consists of several steps involving the formation of the cycloadducts, the 6-chloro-4-trimethylsilyloxy-2-methoxyspiro[cyclohex-3-en-1,3′-indolin]-2′-one derivatives, transformed into spiro[cyclohexa-2,5-dien-1,3′-indoline]-2′,4-diones via 6-chloro-spiro[cyclohex-2-en-1,3′-indoline]-2′,4-dione intermediates. The reduction of spiro[cyclohexa-2,5-dien-1,3′-indoline]-2′,4-diones gave spiro[cyclohexane-1,3′-indoline]-2′,4-diones 7. Using a ‘one pot reaction’, starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield. 相似文献
15.
Three-component condensation of 6-aminoquinoline with formaldehyde and cyclic β-diketones (cyclohexane-1,3-dione and dimedone) gave new partially hydrogenated benzo[b][4,7]phenanthroline derivatives. An analogous reaction with indan-1,3-dione gave indeno[2,1-b][4,7]phenanthroline derivatives. The products were subjected to oxidative dehydrogenation. 相似文献
16.
5,6-Unsubstituted 1,3-oxazine-2,4-diones ( 3 ) and 6-unsubstituted 5-methyl-1,3-oxazine-2,4-diones ( 4 ) were prepared by reduction of the corresponding 6-chloro derivatives ( 1 and 2 ). Treatment of 6-chloro-3-methyl-1,3-oxazine-2,4-dione ( 1a ) with sodium azide, sodium cyanide, secondary amines and aniline gave the corresponding 6-substituted compounds ( 7, 9, 10 and 11 ) while the reaction of 1a and 2a,b with primary aliphatic amines such as methylamine and ethylamine caused a ring transformation to pyrimidine ring system giving barbituric acids ( 13a-d ). 相似文献
17.
Michael reactions of isopropylidenemalononitrile with cyanothioacetamide (in the presence of 4-methoxyphenacyl bromide), cyclohexane-1,3-dione, and 4-hydroxycoumarin, gave 6-amino-2-(4-methoxy-benzoylmethylsulfanyl)-4,4-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile, 2-amino-4,4-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, and 2-amino-4,4-dimethyl-5-oxo-4H,5H-pyrano[3,2-c]-chromene-3-carbonitrile, respectively. In the reaction of isopropylidenemalononitrile with cyanoacetamide, only dimerization product of the former, 2-amino-4,6,6-trimethylcyclohexa-2,4-diene-1,1,3-tricarbonitrile, was isolated. Its structure was proved by X-ray analysis. 相似文献
18.
Mal'kina A. G. Skvortsov Yu. M. Moshchevitina E. I. Bel'skii V. K. Trofimov B. A. 《Chemistry of Heterocyclic Compounds》1992,28(3):279-282
A simple method for the synthesis of 5,5-dimethyl-4-cyanomethylene-2-cyanomethyl-2-[1-methyl-1-(carbamoyloxy)ethyl]-1,3-dithiolanes was developed on the basis of the reaction of 5,5-dimethyl-4-cyanomethylene-1,3-oxathiolan-2-one with amines (primary and secondary) and ammonia.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 335–338, March, 1992. 相似文献
19.
Majid M. Heravi Hamideh Alinejhad Zohreh Daroogheha Fatemeh F. Bamoharram Fatemeh Derikvand 《合成通讯》2013,43(15):2191-2200
An efficient synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives was reported via four-component coupling reaction of aldehydes, dimedone, 1,3-indandione, and amines in refluxing ethanol or three-component condensation of aldehydes, 1,3-indandione, and 5,5-dimethyl-3-arylamino-cyclohex-2-enone derivatives at 120 °C under solvent-free conditions in the presence of a catalytic amount of Preyssler-type heteropolyacid, H14[NaP5W30O110], as a green and reusable catalyst. 相似文献
20.
Beermohamed VinoshaSubbu Perumal Subbiah RenugaAbdulrahman I. Almansour 《Tetrahedron letters》2012,53(8):962-966
A facile protocol for the stereoselective construction of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3-d]pyrimidines from the reactions of 2,2′-sulfonylbis(1,3-diarylprop-2-en-1-ones) with cyclic 1,3-diketones, viz. cyclohexane-1,3-diones, barbituric acid, and 2-thioxodihydropyrimidine-4,6(1H,5H)-dione in the presence of DBU in ethanol is described. This transformation presumably occurs via domino Michael addition-proton exchange-annulation via intramolecular displacement sequence. 相似文献