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1.
Reactions of aromatic aldehydes with cyanothioacetamide and dimethyl malonate in the presence ofN-methylmorpholine affordedN-methylmorpholinium 4-aryl-5-cyano-3-methoxycarbonyl-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates. The latter were used to
synthesize substituted 6-(alkylthio)-2-oxo-1,2,3,4-tetrahydropyridines.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 485–487, March, 2000. 相似文献
2.
V. V. Shchepin A. E. Korzun M. I. Vakhrin S. N. Shurov P. S. Silaichev M. A. Ezhikova M. I. Kodess 《Russian Journal of General Chemistry》2005,75(12):1935-1938
Zinc enolates formed from 1-aryl-2-bromo-2-phenylethanones and zinc react with dimethyl 2-(1-arylmethylene)malonates to afford dimethyl 2-(1,3-diaryl-3-oxo-2-phenylpropyl)malonates. The latter react with cyclohexylamine, piperidine, or morpholine to give the corresponding monosubstituted amides. The zinc enolate derived from 2-bromoindanone and zinc reacts with dimethyl 2-(4-bromobenzylidene)malonate, yielding dimethyl 2-[(4-bromophenyl)(1-oxoindan-2-yl)methyl]malonate. The final products largely form as a single diastereomer. 相似文献
3.
Rajeshwar Reddy Sagyam Himabindu Vurimidi Pratap Reddy Padi Katkam Srinivas 《合成通讯》2013,43(15):2232-2240
An unexpected synthesis of highly substituted indole derivatives was provided by treating 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-pentanoic acid phenylamide with aryl hydrazines in the presence of trifluoroacetic acid in tetrahydrofuran. 相似文献
4.
A. A. Yavolovskii Yu. E. Ivanov L. V. Grishchuk V. Kh. Kravtsov M. S. Fonar’ G. L. Kamalov 《Russian Journal of Organic Chemistry》2018,54(8):1213-1217
Reaction of potassium thiocyanate with 2-[2-oxo-1-(1-tosyloxyimino)-2-phenylethyl]pyrimidin-4-(3H)-one derivatives led to the formation of a new fused heterocyclic system with a common nitrogen atom, substituted 7H-[1,2,5]thiadiazolo[2,3-a]pyrimidin-7-one. 相似文献
5.
V. A. Vasin I. Yu. Bolusheva V. V. Razin N. V. Somov 《Russian Journal of Organic Chemistry》2014,50(7):993-1002
β-Bromo-β-(methylsulfonyl)styrene reacted with dimethyl malonate and methyl cyanoacetate in the presence of sodium hydride to give sulfonyl-substituted cyclopropanes, and sulfonyl-substituted 2,3-dihydrofuran was also formed in the reaction with methyl acetoacetate. Reactions of α-bromo-β-(bromomethylsulfonyl) styrene with dimethyl malonate and methyl cyanoacetate led to the formation of 2,3-dihydro-λ6-thiophene S,S-dioxide derivatives. In the reaction of α-bromo-β-(bromomethylsulfonyl)styrene with methyl acetoacetate, 2,3-dihydro-λ6-thiophene S,S-dioxide and 2,5-dihydro-λ6-thiophene S,S-dioxide derivatives and methyl acetoacetate O-alkylation product, methyl 3-[(E)-2-(bromomethylsulfonyl)-1-phenylvinyloxy]but-2-enoate, were obtained at a ratio of 2.7: 1.2: 1. α-Bromo-β-(methylsulfonyl)styrene reacted with dimethyl malonate to produce dimethyl 2-[2-(methylsulfonyl)-1-phenylethylidene]malonate. The reaction of β-bromo-β-(bromomethylsulfonyl) styrene with dimethyl malonate and methyl cyanoacetate were strictly stereoselective, and they afforded tetrahydro-λ6-thiophene S,S-dioxide derivatives. The reaction of the same substituted styrene with methyl acetoacetate was not stereoselective, and the products were two diastereoisomeric tetrahydro-λ6-thiophene S,S-dioxides and sulfonyl-substituted 2,3-dihydrofuran at a ratio of 2.3: 2.7: 1. 相似文献
6.
Tina S. Guion Madlene U. Koller Rene J. Lachicotte Robin N. Rutledge Karen C. Hildebran Phuong H. Le 《合成通讯》2013,43(9):1753-1762
ortho-Toluic acid was dimetalated with excess lithium diisopropylamide, and the resulting intermediate was condensed with a variety of aromatic esters to afford new substituted 2-(2-oxo-2-phenylethyl)benzoic acids (ortho-phenacylbenzoic acids). 相似文献
7.
Several amide oximes underwent condensation reactions with dimethyl acetylene dicarboxylate to afford 1:1 adducts. Under basic conditions, these adducts underwent ring closure to afford several methyl [3-(substituted)-4,5-dihydro-5-oxo-6H-1,2,4-oxadiazin-6-ylidene]acetates. The reactions of these compounds with a variety of amines resulted in addition-rearrangement reactions with the formation of the corresponding methyl 2-substituted-5-substituted amino-1,6-dihydro-6-oxo-4-pyrimidine carboxylates. 相似文献
8.
A. G. Balya A. N. Vasilenko V. S. Brovarets B. S. Drach 《Russian Journal of General Chemistry》2008,78(11):2125-2131
N-(1-Chloro-2-oxo-2-phenylethyl)acet-, -benz-, and -4-methylbenzamides reacted with thiosemicarbazides and aromatic aldehyde thiosemicarbazones to give derivatives of 5-amino-2-hydrazino-1,3-thiazole. The latter underwent recyclization and acid hydrolysis on heating with hydrochloric acid to produce substituted 3-amino-2-thiohydantoins. 相似文献
9.
Alaa A. Hassan Fathy F. Abdel-Latif Mohamed Abdel Aziz Sara M. Mostafa Stefan Bräse Martin Nieger 《Chemical Papers》2015,69(7):973-982
A facile and rapid procedure for the synthesis of dimethyl-2-[3-amino-5-(2-methoxy-2-oxoethylidene)-4-oxothiazolidin-2-ylidenehydrazono]succinate, dimethyl {[2-alkylidenehydrazono)-5-(2-methoxy-2-oxoethylidene)-4-oxothiazolidin-3-yl)amino]succinate and methyl (4-amino-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-yl)acetate affording yields of 61–54 %, 22–18 % and 14–11 %, respectively, via a condensation reaction of dimethyl acetylenedicarboxylate (DMAD) with (substituted ylidene)thiocarbonohydrazides. One of the products was conclusively confirmed by single-crystal X-ray analysis. A mechanism for the formation of the products is presented. 相似文献
10.
《Tetrahedron: Asymmetry》2005,16(6):1183-1187
The asymmetric palladium-catalyzed benzylic reaction of 1-(2-naphthyl)ethyl acetate and its 6-methoxy substituted analogue with dimethyl malonate anion led to substitution products with up to 90% ee when the iPr-DUPHOS chiral ligand was used. 相似文献
11.
V. V. Shchepin A. E. Korzun M. I. Vakhrin P. S. Silaichev M. A. Ezhikova M. I. Kodess 《Russian Journal of General Chemistry》2006,76(5):777-780
Zinc enolates derived from 1-aryl-2-bromo-2-phenylethanone react with alkyl 2-oxochromene-3-carboxylates and methyl 6-bromo-2-oxochromene-3-carboxylate to give, respectively, alkyl 4-(2-aryl-2-oxo-1-phenylethyl)-2-oxochroman-3-carboxylates and methyl 6-bromo-4-(2-aryl-2-oxo-1-phenylethyl)-2-oxochroman-3-carboxylate as a single stereoisomer. Zinc enolates derived from 2-bromoindan-1-one react with alkyl 2-oxochromene-3-carboxylates to give alkyl 2-oxo-4-(1-oxoindan-2-yl)chroman-3-carboxylates as a single stereoisomer. 相似文献
12.
Ivachtchenko AV Kobak VV Ilyn AP Khvat AV Kysil VM Williams CT Kuzovkova JA Kravchenko DV 《Journal of combinatorial chemistry》2005,7(2):227-235
Two efficient strategies for solution-phase parallel synthesis of libraries of quinoline derivatives are described. The first synthetic pathway features the Pfitzinger reaction of isatin with diethyl malonate and sulfochlorination of the resulting 2-oxo-1,2-dihydroquinoline-4-carboxylate followed by generation of sulfonamide library. The second strategy employs the unusual behavior of 5-sulfamoylisatins in Pfitzinger reactions, which results in formation of 6-sulfamoyl-4-carboxyquinolines instead of the anticipated 2-oxo-1,2-dihydroquinoline structures. The obtained carboxylates appeared to be convenient synthetic intermediates for the generation of the corresponding carboxamide libraries. Using these reagents, the parallel solution-phase synthesis of more than 500 substituted quinoline and 2-oxo-1,2-dihydroquinoline derivatives has been accomplished on the 50-100-mg scale. Simple manual techniques for parallel reactions using special CombiSyn synthesizers were coupled with easy purification procedures to give high-purity final products. The scope and limitations of the developed approaches are discussed. 相似文献
13.
D. V. Shishkin N. Z. Baibulatova A. N. Lobov S. P. Ivanov L. V. Spirikhin V. A. Dokichev 《Chemistry of Natural Compounds》2010,46(1):62-65
Diastereomers of N(12)-(2-hydroxy-2-phenylethyl)cytisine were synthesized by reduction of N(12)-(2-oxo-2-phenylethyl)cytisine
by Yamamoto reagent. Their structures were solved using x-ray structure analysis. 相似文献
14.
A. D. Dyachenko S. M. Desenko V. D. Dyachenko A. N. Chernega 《Chemistry of Heterocyclic Compounds》2004,40(8):1009-1016
The condensation of cyclohexylidenemalononitrile or cyclohexylidenecyanoacetic ester with thioamidoethyl(methyl)malonate in the presence of sodium ethylate gave 6-amino-3-carbethoxy-5-cyano-4-spirocyclohexane-1,2,3,4-tetrahydropyridine-2-thione and 3-carbethoxy(methoxy)-5-cyano-6-oxo-4-spirocyclohexanepiperidine-2-thiones which were used in the synthesis of the corresponding substituted 2-alkylthiotetrahydropyridines. 5-Carbethoxy-3-cyano-3-methyl-6-methylthio-4-spiro-cyclohexane-3,4-dihydropyridine-2(1H)-one was studied by X-ray crystallography. 相似文献
15.
V. B. Vol’eva I. S. Belostotskaya N. L. Komissarova L. N. Kurkovskaya 《Russian Journal of Organic Chemistry》2008,44(6):803-806
Products of the reactions of 4- and 2-hydroxy-3,5-di-tert-butyl-benzaldehydes with malonic acid, diethyl malonate, and acetic anhydride in the presence of weak bases were isolated and identified. The reactions of 3,5-di-tert-butyl-4-hydroxybenzaldehyde with malonic acid and acetic anhydride in the presence of sodium acetate and piperidine gave 3,5-di-tert-butyl-4-hydroxycinnamic acid. The reaction of its 2-hydroxy isomer with acetic anhydride stopped at the stage of formation of the corresponding O-acetyl derivative, while in the reaction with malonic acid the corresponding substituted cinnamic acid and its lactone (coumarin derivative) were formed as intermediate products in a transformation sequence finally leading to 3-(3,5-di-tertbutyl-2-hydroxyphenyl)-3-piperidinopropionic acid and 6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid. Analogous differences were typical of reactions of isomeric 4- and 2-hydroxy-3,5-di-tert-butylbenzaldehydes with diethyl malonate. The transformations of the 2-hydroxy isomer were accompanied by hydrolysis and formation of an adduct of intermediate coumarin derivative with diethyl malonate and piperidine. 相似文献
16.
V. V. Shchepin S. V. Nikitin S. A. Filimonov N. Yu. Russkikh P. S. Silaichev 《Russian Journal of Organic Chemistry》2007,43(10):1432-1436
Zinc enolates generated from dimethyl 4-bromo-2,2-dimethyl-3-oxohexane-1,6-dioate and zinc reacted with aromatic aldehydes giving methyl 2,2-dimethyl-3-oxo-3-(5-oxo-2-aryltetrahydrofuran-3-yl)propanoates. The reaction of zinc enolates obtained from dimethyl 4-bromo-2,2-dimethyl-3-oxoheptane-1,7-dioate and zinc with aromatic aldehydes depending on the synthesis conditions led to the formation either methyl 2,2-dimethyl-3-oxo-3-(6-oxo-2-aryltetrahydropyran-3-yl)propanoates or 3-(5,5-dimethyl-4,6-dioxo-2-aryltetrahydropyran-3-yl)propanoates. The compounds synthesized formed as a single diastereomer of E-configuration. 相似文献
17.
T. I. Reznikova A. Ya. Tikhonov L. B. Volodarskii 《Chemistry of Heterocyclic Compounds》1986,22(4):417-421
N-(2-Oxoalkyl)-2-chloroacetohydroxamic acids were obtained by acylation of 1,2-hydroxylamino ketones with chloroacetyl chloride. Their reaction with urotropin and sodium azide gives urotropinium salts and acetoxyhydroxamic acid azides. 1-Hydroxy-2-oxo-1,2,3,6-tetrahydropyrazines were obtained by treating N-(2-oxoalkyl)-2-chloroacetohydroxyamic acids with ammonia, and also by reacting the urotropinium salts and azides of acetohydroxamic acids with hydrochloric acid and triphenylphosphine, respectively. The reaction of N-(1-methyl-2-oxo-2-phenylethyl)-2-chloroacetohydroxamic acid with urotropin in an acid medium leads to the formation of 6-methyl-2-oxo-5-phenyl-1,2-dihydropyrazine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 509–513, April, 1986. 相似文献
18.
Mono and 1,3-disubstituted selenoureas react with dimethyl acetylenedicarboxylate to give in high yield substituted 3,4-dihydro-4-oxo-2H-1,3-selenazines whose structures were established by speclroscopic methods. 相似文献
19.
S. Munavalli D. K. Rohrbaugh G. W. Wagner F. R. Longo H. D. Durst 《Phosphorus, sulfur, and silicon and the related elements》2013,188(4):781-789
Microwave catalyzed reaction of a neat mixture of styrene oxide and H-dimethylphosphonate furnished dimethyl methylphosphonate, trimethylphosphate, phenylacetaldehyde, 1-methoxy-2-phenylethanol, 1-phenylethleneglycol, cis- and trans-1,3-diphenylcyclobutanes, hydrogen 1-(2-phenylethyl)methylphosphinate, (1-phenylethyl)dimethylphosphonate, and (1-phenylethyl)dimethylphosphonate via free radical processes. 相似文献
20.
The reaction of 4-bromo-1,3-diphenyl-2-buten-1-one with thiourea or N,N′-diphenylthiourea gives 2-(2-amino-4-phenyl-4,5-dihydro-1,3-thiazol-4-yl)-and
2-[3,4-diphenyl-2-(phenylimino)-1,3-thiazolidin-4-yl]-1-phenyl-1-ethanone — the products of nucleophilic substitution of the
halogen atom and Michael addition at position 3 of the 2-buten-1-one system. A similar reaction with thiosemicarbazide and
1-phenylthiosemicarbazide gives the 4-(2-oxo-2-phenylethyl)-4-phenyl-and 4-(2-oxo-2-phenylethyl)-3,4-diphenyl-1,3-thiazolidin-2-one
hydrobromides respectively.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 103–110, January, 2008. 相似文献