Pd-Catalyzed Benzylic C-H Amidation with Benzyl Alcohols in Water: A Strategy To Construct Quinazolinones

被引：200

作者：

Hikawa, Hidemasa ^{[1
]}

Ino, Yukari ^{[1
]}

Suzuki, Hideharu ^{[1
]}

Yokoyama, Yuusaku ^{[1
]}

机构：

[1] Toho Univ, Fac Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 16期

关键词：

ONE-POT SYNTHESIS; DRY MEDIA; DERIVATIVES; EFFICIENT; RECEPTOR; SYSTEM; 4(3H)-QUINAZOLINONES; CARBONYLATION; CONVERSIONS; CYCLIZATION;

D O I：

10.1021/jo301282n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the synthesis of 4-phenyl-quinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C-H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (eta(3)-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.

引用

页码：7046 / 7051

页数：6

共 45 条

[31] Auto-redox reaction:: Tin(II) chloride-mediated one-step reductive cyclization leading to the synthesis of novel biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity [J].

Roy, AD ;

Subramanian, A ;

Roy, R .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :382-385

[32] Mechanism of Pd(OAc)2/DMSO-catalyzed aerobic alcohol oxidation:: Mass-transfer-limitation effects and catalyst decomposition pathways [J].

Steinhoff, BA ;

Stahl, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) :4348-4355

[33] Synthesis and in vitro evaluation of derivatives of the β1-adrenergic receptor antagonist HX-CH 44 [J].

Stephenson, Karin A. ;

Wilson, Alan A. ;

Houle, Sylvain ;

Vasdev, Neil .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (18) :5506-5509

[34] Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion [J].

Thu, Hung-Yat ;

Yu, Wing-Yiu ;

Che, Chi-Ming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) :9048-9049

[35] Catalytic conversions in water, part 8: carbonylation and hydrocarboxylation reactions catalyzed by palladium trisulfonated triphenylphosphine complexes [J].

Verspui, G ;

Papadogianakis, G ;

Sheldon, RA .

CATALYSIS TODAY, 1998, 42 (04) :449-458

[36] Efficient synthesis and fluorescence properties of highly functionalized 2-aryl-quinazolin-4(3H)-ones [J].

Waibel, Michael ;

Hasserodt, Jens .

TETRAHEDRON LETTERS, 2009, 50 (23) :2767-2769

[37] Synthesis of 2-Arylquinazolin-4(3H)-one Derivatives Catalyzed by Iodine in [bmim+][BF-4] [J].

Wang, Xiang-Shan ;

Yang, Ke ;

Zhang, Mei-Mei ;

Yao, Chang-Sheng .

SYNTHETIC COMMUNICATIONS, 2010, 40 (17) :2633-2646

[38] Antitumor agents. Part 204: Synthesis and biological evaluation of substituted 2-aryl quinazolinones [J].

Xia, Y ;

Yang, ZY ;

Hour, MJ ;

Kuo, SC ;

Xia, P ;

Bastow, KF ;

Nakanishi, Y ;

Nampoothiri, P ;

Hackl, T ;

Hamel, E ;

Lee, KH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (09) :1193-1196

[39] Palladium-Catalyzed Intermolecular Directed C-H Amidation of Aromatic Ketones [J].

Xiao, Bin ;

Gong, Tian-Jun ;

Xu, Jun ;

Liu, Zhao-Jing ;

Liu, Lei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) :1466-1474

[40] Palladium-catalyzed allylic C-H amination of alkenes with N-fluorodibenzenesulfonimide: water plays an important role [J].

Xiong, Tao ;

Li, Yan ;

Mao, Lujia ;

Zhang, Qian ;

Zhang, Qian .

CHEMICAL COMMUNICATIONS, 2012, 48 (16) :2246-2248

← 1 2 3 4 5 →