An Expedient and Divergent Tandem One-Pot Synthesis of Pyrimidin-2,4-diones Using the Blaise Reaction Intermediate

被引：32

作者：

Chun, Yu Sung ^{[1
]}

Xuan, Zi ^{[1
]}

Kim, Ju Hyun ^{[1
]}

Lee, Sang-gi ^{[1
]}

机构：

[1] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

关键词：

C-H ARYLATION; REGIOSELECTIVE SYNTHESIS; ORGANIC-SYNTHESIS; GENERAL-METHOD; URACILS; ENAMINOESTERS; DERIVATIVES; INHIBITORS; MECHANISM; DISCOVERY;

D O I：

10.1021/ol401389j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel divergent tandem one-pot method for the synthesis of 3,5,6-trisubstituted 1H-pyrimidin-2,4-dione derivatives Is developed. In the presence of 10 mol % of Cu(OAc)(2), the alpha-substituted Blaise reaction intermediates (R-2 not equal H) reacted with Isocyanates chemoselectively to afford pyrimidin-2,4-diones, whereas the alpha-unsubstituted Blaise reaction intermediate (R-2 = H) showed a propensity to be a C-nucleophile toward electrophiles, permitting the installation of different functionalities at the 5-position through sequential tandem reactions.

引用

页码：3162 / 3165

页数：4

共 49 条

[1] Synthesis of modified uracil and cytosine nucleobases using a microwave-assisted method [J].

Burgula, Laxmi Narayana ;

Radhakrishnan, K. ;

Kundu, Lal Mohan .

TETRAHEDRON LETTERS, 2012, 53 (21) :2639-2642

[2] Generating diverse skeletons of small molecules combinatorially [J].

Burke, MD ;

Berger, EM ;

Schreiber, SL .

SCIENCE, 2003, 302 (5645) :613-618

[3] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].

Campeau, Louis-Charles ;

Stuart, David R. ;

Leclerc, Jean-Philippe ;

Bertrand-Laperle, Megan ;

Villemure, Elisia ;

Sun, Ho-Yan ;

Lasserre, Sandrine ;

Guimond, Nicolas ;

Lecavallier, Melanie ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306

[4] New Strategy for the Synthesis of 1,3-Disubstituted Uracils [J].

Cao, Jian ;

Huang, Xian .

SYNTHETIC COMMUNICATIONS, 2009, 39 (02) :205-214

[5] Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C-H Arylation Reactions [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :9048-9054

[6] Direct C-H arylation of purines:: Development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

ORGANIC LETTERS, 2006, 8 (23) :5389-5392

[7] Intramolecular Direct C-H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2302-2308

[8] Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5-and 6-Aryluracil Bases [J].

Cernova, Miroslava ;

Cerna, Igor ;

Pohl, Radek ;

Hocek, Michal .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13) :5309-5319

[9] Switching the Regioselectivity of Direct C-H Arylation of 1,3-Dimethyluracil [J].

Cernova, Miroslava ;

Pohl, Radek ;

Hocek, Michal .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) :3698-3701

[10] The first chemoselective tandem acylation of the Blaise reaction intermediate: a novel method for the synthesis of α-acyl-β-enamino esters, key intermediate for pyrazoles [J].

Chun, Yu Sung ;

Lee, Ki Kon ;

Ko, Young Ok ;

Shin, Hyunik ;

Lee, Sang-gi .

CHEMICAL COMMUNICATIONS, 2008, (41) :5098-5100

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