Heterocyclization of N-(1-chloro-2,2,2-trifluoroethylidene)carbamates with β-enaminoesters-a novel synthetic strategy to functionalized trifluoromethylated pyrimidines

被引：26

作者：

Sukach, Volodymyr A. ^{[1
]}

Tkachuk, Viktor M. ^{[1
]}

Rusanov, Eduard B. ^{[1
]}

Roeschenthaler, Gerd-Volker ^{[2
]}

Vovk, Mykhaylo V. ^{[2
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine

[2] Jacobs Univ Bremen, Sch Sci & Engn, D-28759 Bremen, Germany

来源：

TETRAHEDRON | 2012年 / 68卷 / 40期

关键词：

Pyrimidines; Heterocyclization; Enamines; Trifluoromethyl group; N-(1-Chloro-2,2,2-trifluoroethylidene)carbamates; 1-CHLOROALKYL ISOCYANATES; 1-CHLOROBENZYL ISOCYANATES; ACID-ESTERS; HETEROCUMULENES; CYCLOCONDENSATION; DERIVATIVES; C; O; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; N-BINUCLEOPHILES; O-BINUCLEOPHILES;

D O I：

10.1016/j.tet.2012.07.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic strategy to 4-trifluoromethyl substituted 2-oxo-1,2-dihydropyrimidine-5-carboxylates has been developed based on the cyclocondensation of beta-enaminoesters with N-(1-chloro-2,2,2trifluoroethylidene)carbamates. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：8408 / 8415

页数：8

共 61 条

[21] Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules [J].

Kirk, Kenneth L. .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :1013-1029

[22]

Koike T, 1999, CHEM PHARM BULL, V47, P128

[23] Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: XIII. Synthesis of dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates and their reaction with arylhydroxymoyl chlorides [J].

Kushnir, O. V. ;

Mel'nichenko, N. V. ;

Vovk, M. V. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (11) :1727-1732

[24] Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: X. 1-Chloroalkyl isocyanates in the synthesis of new 5-aroyldihydropyrimidines [J].

Kushnir, O. V. ;

Sukach, V. A. ;

Vovk, M. V. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (05) :755-761

[25]

Lednicer D., 2008, ORGANIC CHEM DRUG SY, V7, P121

[26] Evaluation of secondary amide replacements in a series of CCR5 antagonists as a means to increase intrinsic membrane permeability. Part 1: Optimization of gem-disubstituted azacycles [J].

Lemoine, Remy C. ;

Petersen, Ann C. ;

Setti, Lina ;

Wanner, Jutta ;

Jekle, Andreas ;

Heilek, Gabrielle ;

deRosier, Andre ;

Ji, Changhua ;

Berry, Pamela ;

Rotstein, David .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (02) :704-708

[27] Pd- and Ni-Catalyzed Cross-Coupling Reactions of Functionalized Organozinc Reagents with Unsaturated Thioethers [J].

Melzig, Laurin ;

Metzger, Albrecht ;

Knochel, Paul .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) :2948-2956

[28] Novel 2-(4-methylsulfonylphenyl)pyrimidine derivatives as highly potent and specific COX-2 inhibitors [J].

Orjales, Aurelio ;

Mosquera, Ramon ;

Lopez, Beatriz ;

Olivera, Roberto ;

Labeaga, Luis ;

Nunez, M. Teresa .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (05) :2183-2199

[29]

Petrov V.A., 2009, FLUORINATED HETEROCY

[30] Selective GlyT1 Inhibitors: Discovery of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a Promising Novel Medicine To Treat Schizophrenia [J].

Pinard, Emmanuel ;

Alanine, Alexander ;

Alberati, Daniela ;

Bender, Markus ;

Borroni, Edilio ;

Bourdeaux, Patrick ;

Brom, Virginie ;

Burner, Serge ;

Fischer, Holger ;

Hainzl, Dominik ;

Halm, Remy ;

Hauser, Nicole ;

Jolidon, Synese ;

Lengyel, Judith ;

Marty, Hans-Peter ;

Meyer, Thierry ;

Moreau, Jean-Luc ;

Mory, Roland ;

Narquizian, Robert ;

Nettekoven, Mathias ;

Norcross, Roger D. ;

Puellmann, Bernd ;

Schmid, Philipp ;

Schmitt, Sebastien ;

Stalder, Henri ;

Wermuth, Roger ;

Wettstein, Joseph G. ;

Zimmerli, Daniel .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (12) :4603-4614

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