Quinazolinone-Directed C-H Activation: A Novel Strategy for the Acetoxylation-Methoxylation of the Arenes

被引：43

作者：

Reddy, B. V. Subba ^{[1
]}

Narasimhulu, G. ^{[1
]}

Umadevi, N. ^{[1
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNLETT | 2012年 / 09期

关键词：

2-aryl-4-quinazolinone; hypervalent iodine reagent; acetoxylation; C-H activation; ARYLATION; DERIVATIVES; BOND; AGENTS; ANTAGONISTS; SP(2);

D O I：

10.1055/s-0031-1290962

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aryl-4-quinazolinones undergo smooth acetoxylation in the presence of 5 mol% Pd(OAc)(2) and a stoichiometric amount of PhI(OAc)(2) via C-H activation to produce the corresponding acetoxy-substituted 4(3H)-quinazolinone derivatives in good yields with high regioselectivity.

引用

页码：1364 / 1370

页数：7

共 45 条

[1] A novel method for the synthesis of 4(3H)-quinazolinones [J].

Abdel-Jalil, RJ ;

Voelter, W ;

Saeed, M .

TETRAHEDRON LETTERS, 2004, 45 (17) :3475-3476

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[4]

Buchanan J.G., 1972, SELECTIVE ORGANIC TR, V2, P1

[5] Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].

Cai, Guixin ;

Fu, Ye ;

Li, Yizhou ;

Wan, Xiaobing ;

Shi, Zhangjie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673

[6] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].

Chen, X ;

Li, JJ ;

Hao, XS ;

Goodhue, CE ;

Yu, JQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79

[7] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].

Chen, Xiao ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635

[8] PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes [J].

Chernyak, Natalia ;

Dudnik, Alexander S. ;

Huang, Chunhui ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8270-+

[9] Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors [J].

Corbett, JW ;

Ko, SS ;

Rodgers, JD ;

Gearhart, LA ;

Magnus, NA ;

Bacheler, LT ;

Diamond, S ;

Jeffrey, S ;

Klabe, RM ;

Cordova, BC ;

Garber, S ;

Logue, K ;

Trainor, GL ;

Anderson, PS ;

Erickson-Viitanen, SK .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) :2019-2030

[10] Anilide ortho-arylation by using C-H activation methodology [J].

Daugulis, O ;

Zaitsev, VG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4046-4048

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