Synthesis of 4-Quinolones through Nickel-Catalyzed Intramolecular Amination on the β-Carbon of o-(N-Alkylamino)propiophenones

被引：15

作者：

Ueno, Satoshi ^{[1
]}

Shimizu, Ryosuke ^{[1
]}

Maeda, Ryohei ^{[1
]}

Kuwano, Ryoichi ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan

来源：

SYNLETT | 2012年 / 11期

关键词：

nickel; cyclization; amination; ketones; oxidation; SUGASAWA REACTION; 2-ARYL-4-QUINOLONES; 4-HYDROXYQUINOLINE; CYCLIZATION; AMIDATION; INHIBITOR; ANILINES; MILD;

D O I：

10.1055/s-0031-1291146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

o-(N-Alkylamino)propiophenones are converted into 4-quinolones in the presence of chlorobenzene, potassium phosphate, morpholine, and nickel(0) catalyst. The reaction proceeds through the nickel-catalyzed formation of beta-enaminones from o-(N-alkylamino)propiophenones and morpholine, followed by the intramolecular transamination.

引用

页码：1639 / 1642

页数：4

共 22 条

[11] Palladium-Catalyzed Dehydrogenative β′-Functionalization of β-Keto Esters with Indoles at Room Temperature [J].

Leskinen, Mikko V. ;

Yip, Kai-Tai ;

Valkonen, Arto ;

Pihko, Petri M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) :5750-5753

[12] Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters [J].

Nakamura, S ;

Kozuka, M ;

Bastow, KF ;

Tokuda, H ;

Nishino, H ;

Suzuki, M ;

Tatsuzaki, J ;

Natschke, SLM ;

Kuo, SC ;

Lee, KH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (14) :4396-4401

[13] Dehydrogenative [4+2] Cycloaddition of Formamides with Alkynes through Double C-H Activation [J].

Nakao, Yoshiaki ;

Morita, Eiji ;

Idei, Hiroaki ;

Hiyama, Tamejiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3264-3267

[14] KINETICS AND MECHANISM OF FORMATION OF 4-HYDROXYQUINOLINE FROM METHYL ANTHRANILATE [J].

OGATA, Y ;

KAWASAKI, A ;

TSUJIMUR.K .

TETRAHEDRON, 1971, 27 (13) :2765-&

[15] Design of new reaction conditions for the Sugasawa reaction based on mechanistic insights [J].

Prasad, K ;

Lee, GT ;

Chaudhary, A ;

Girgis, MJ ;

Streemke, JW ;

Repic, O .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (05) :723-732

[16] Novel HIV-1 integrase inhibitors derived from quinolone antibiotics [J].

Sato, M ;

Motomura, T ;

Aramaki, H ;

Matsuda, T ;

Yamashita, M ;

Ito, Y ;

Kawakami, H ;

Matsuzaki, Y ;

Watanabe, W ;

Yamataka, K ;

Ikeda, S ;

Kodama, E ;

Matsuoka, M ;

Shinkai, H .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (05) :1506-1508

[17]

Son JK, 2001, HETEROCYCLES, V55, P1981

[18] AMINOHALOBORANE IN ORGANIC-SYNTHESIS .1. SPECIFIC ORTHO SUBSTITUTION-REACTION OF ANILINES [J].

SUGASAWA, T ;

TOYODA, T ;

ADACHI, M ;

SASAKURA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (15) :4842-4852

[19] Nickel-Catalyzed Formation of a Carbon-Nitrogen Bond at the β Position of Saturated Ketones [J].

Ueno, Satoshi ;

Shimizu, Ryosuke ;

Kuwano, Ryoichi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (25) :4543-4545

[20] Nickel-Catalyzed Decarboxylative Carboamination of Alkynes with Isatoic Anhydrides [J].

Yoshino, Yasufumi ;

Kurahashi, Takuya ;

Matsubara, Seijiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7494-+

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