Microwave assisted sp3 C-H activation of 2-methyl-quinoline and addition to electron deficient ketones

被引：0

作者：

Rao, Nalajala Nageswara ^{[1
]}

Mali, Prakash Rambhau ^{[1
]}

Meshram, H. M. ^{[1
]}

机构：

[1] CSIR, Indian Inst Chem Technol, Med Chem & Pharmacol Div, Hyderabad 500007, Andhra Pradesh, India

来源：

INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2014年 / 53卷 / 09期

关键词：

Catalyst-free; ketone; microwave; 2-methyl-quinoline; water; AZAARENE-SUBSTITUTED; 3-HYDROXY-2-OXINDOLES; BOND; FUNCTIONALIZATION;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst-free aqueous mediated nucleophilic addition of 2-methyl-quinolines with various ketones has been performed under microwave irradiation. The substrates alpha,beta-unsaturated ketones and diketones on reaction with methyl aza-arenes give selectively, 1,2-addition and mono addition products respectively with good yields. A significant improvement in this protocol is isatin which gives 3-substituted-3-hydroxy substituted product instead of bis(quinolin-2-ylmethyl) indolin-2-one derivatives. The whole protocol fulfils the principle of green chemistry and sustainability, minimizing the use of organic solvents and generation of any type of wastes.

引用

收藏

页码：1153 / 1158

页数：6

相关论文

共 28 条

[1] Ruthenium(II)-catalyzed selective monoarylation in water and sequential functionalisations of C-H bonds [J].

Arockiam, Percia B. ;

Fischmeister, Cedric ;

Bruneau, Christian ;

Dixneuf, Pierre H. .

GREEN CHEMISTRY, 2013, 15 (01) :67-71

[2] Highly chemoselective addition of amines to epoxides in water [J].

Azizi, N ;

Saidi, MR .

ORGANIC LETTERS, 2005, 7 (17) :3649-3651

[3]

BAXTER PNW, 1994, ANGEW CHEM INT EDIT, V33, P2284, DOI 10.1002/anie.199422841

[4] C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].

Chen, David Y. -K. ;

Youn, So Won .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474

[5] Multicomponent reactions in unconventional solvents: state of the art [J].

Gu, Yanlong .

GREEN CHEMISTRY, 2012, 14 (08) :2091-2128

[6] Efficient [5+1]-strategy for the assembly of 1,8-naphthyridin-4(1H)-ones by domino amination/conjugate addition reactions of 1-(2-chloropyridin-3-yl) prop-2-yn-1-ones with amines [J].

Iaroshenko, Viktor O. ;

Knepper, Ingo ;

Zahid, Muhammad ;

Kuzora, Rene ;

Dudkin, Sergii ;

Villinger, Alexander ;

Langer, Peter .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) :2955-2959

[7] Copper-catalysed addition of α-alkyl azaarenes to ethyl glyoxylate via direct C(sp3)-H activation [J].

Jin, Jia-Jia ;

Niu, Hong-Ying ;

Qu, Gui-Rong ;

Guo, Hai-Ming ;

Fossey, John S. .

RSC ADVANCES, 2012, 2 (14) :5968-5971

[8] Water as catalyst and solvent: Tetrahydropyranylation of alcohols in an aqueous medium [J].

Kavala, V ;

Samal, AK ;

Patel, BK .

ARKIVOC, 2005, :20-29

[9] Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water [J].

Khatik, Gopal L. ;

Kumar, Raj ;

Chakraborti, Asit K. .

ORGANIC LETTERS, 2006, 8 (11) :2432-2436

[10] Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes: Addition to Enones [J].

Komai, Hirotomo ;

Yoshino, Tatsuhiko ;

Matsunaga, Shigeki ;

Kanai, Motomu .

ORGANIC LETTERS, 2011, 13 (07) :1706-1709