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

[11] Cu(OAc)2-Catalyzed Tandem Blaise/Pinner-Type Reaction for One-Pot Synthesis of Pyrimidin-4-ones [J].

Chun, Yu Sung ;

Kim, Ju Hyun ;

Choi, Suh Young ;

Ko, Young Ok ;

Lee, Sang-gi .

ORGANIC LETTERS, 2012, 14 (24) :6358-6361

[12] Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes [J].

Chun, Yu Sung ;

Lee, Jun Hee ;

Kim, Ju Hyun ;

Ko, Young Ok ;

Lee, Sang-gi .

ORGANIC LETTERS, 2011, 13 (24) :6390-6393

[13] Tandem Blaise-Nenitzescu reaction: one-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles [J].

Chun, Yu Sung ;

Ryu, Ka Yeon ;

Kim, Ju Hyun ;

Shin, Hyunik ;

Lee, Sang-gi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (05) :1317-1319

[14] One-Pot Synthesis of 2-Pyridones via Chemo- and Regioselective Tandem Blaise Reaction of Nitriles with Propiolates [J].

Chun, Yu Sung ;

Ryu, Ka Yeon ;

Ko, Young Ok ;

Hong, Joo Yeon ;

Hong, Jongki ;

Shin, Hyunik ;

Lee, Sang-gi .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7556-7558

[15] Tandem Blaise-Alkenylation with Unactivated Alkynes: One-Pot Synthesis of α-Vinylated β-Enaminoesters from Nitriles [J].

Chun, Yu Sung ;

Ko, Young Ok ;

Shin, Hyunik ;

Lee, Sang-gi .

ORGANIC LETTERS, 2009, 11 (15) :3414-3417

[16] Accessing new chemical space for 'undruggable' targets [J].

Dandapani, Sivaraman ;

Marcaurelle, Lisa A. .

NATURE CHEMICAL BIOLOGY, 2010, 6 (12) :861-863

[17] Highlights in the Discovery of Antiviral Drugs: A Personal Retrospective [J].

De Clercq, Erik .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (04) :1438-1450

[18] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].

Denmark, SE ;

Thorarensen, A .

CHEMICAL REVIEWS, 1996, 96 (01) :137-165

[19] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds [J].

Do, Hien-Ouang ;

Khan, Rana M. Kashif ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15185-15192

[20] From Oblivion into the Limelight: Iron (Domino) Catalysis [J].

Fuerstner, Alois .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1364-1367

← 1 2 3 4 5 →