Synthesis of 1,4-diketones:: reaction of α-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE)

被引：26

作者：

Nishiyama, Yutaka ^{[1
]}

Kobayashi, Akihiro ^{[1
]}

机构：

[1] Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 31期

关键词：

D O I：

10.1016/j.tetlet.2006.05.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,4-Diketones were prepared by the reaction of alpha-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE) in moderate to good yields. Similarly, a-bromo esters were reductively coupled using TDAE to give the 1,4-diesters in moderate yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5565 / 5567

页数：3

共 46 条

[1] Nucleophilic trifluoromethylation using trifluoromethyl iodide.: A new and simple alternative for the trifluoromethylation of aldehydes and ketones [J].

Aït-Mohand, S ;

Takechi, N ;

Médebielle, M ;

Dolbier, WR .

ORGANIC LETTERS, 2001, 3 (26) :4271-4273

[2] CHANGE OF REGIOSELECTIVITY IN THE REACTION OF TIN ENOLATES AND ALPHA-BROMO KETONES - SYNTHESIS OF 1,4-DIKETONES UNDER NONRADICAL CONDITIONS [J].

BABA, A ;

YASUDA, M ;

YANO, K ;

SHIBATA, I ;

MATSUDA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3205-3207

[3] RECENT ADVANCES IN CHEMISTRY OF PYRROLE [J].

BALTAZZI, E .

CHEMICAL REVIEWS, 1963, 63 (05) :511-+

[4] SYNTHESIS OF 2,5-DIARYLFURANS FROM PHENACYL BROMIDES [J].

BARBA, F ;

VELASCO, MD ;

GUIRADO, A .

SYNTHESIS-STUTTGART, 1984, (07) :593-595

[5] Tetrakis(dimethylamino)ethylene (TDAE) mediated addition of difluoromethyl anions to heteroaryl thiocyanates.: A new simple access to heteroaryl-SCF2R derivatives [J].

Billard, T ;

Langlois, BR ;

Médebielle, M .

TETRAHEDRON LETTERS, 2001, 42 (20) :3463-3465

[6]

BOSSHARD P, 1966, ADV HETEROCYCL CHEM, V7, P384

[7]

BRISCOE MW, 1994, J CHEM SOC P1, V8, P3115

[8]

BURGER H, 1993, ORGANOMETALLICS, V12, P4930

[9] Synthesis and electron-transfer reactions of some 3-difluoroacetylated imidazo[1,2-α]pyridine derivatives [J].

Burkholder, C ;

Dolbier, WR ;

Médebielle, M ;

Ait-Mohand, S .

TETRAHEDRON LETTERS, 2001, 42 (17) :3077-3080

[10] Tetrakis(dimethylamino)ethylene as a useful reductant of some bromodifluoromethyl heterocycles.: Application to the synthesis of new gem-difluorinated heteroarylated compounds [J].

Burkholder, C ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5385-5394

← 1 2 3 4 5 →