Ruthenium-Catalyzed Regioselective Alkenylation/Tandem Hydroamidative Cyclization of Unmasked Quinazolinones Using Terminal Alkynes

被引：25

作者：

Viveki, Amol B. ^{[1
,2
]}

Mhaske, Santosh B. ^{[1
,2
]}

机构：

[1] Natl Chem Lab, CSIR, Div Organ Chem, Pune 411008, Maharashtra, India

[2] Natl Chem Lab, CSIR, Acad Sci & Innovat Res AcSIR, Pune 411008, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

关键词：

CASCADE SYNTHESIS; DIRECTING GROUP; QUINAZOLIN-4(3H)-ONES; FUNCTIONALIZATION; HYDROARYLATION; BONDS; DIVERSIFICATION; HETEROARENES; CHEMISTRY; ALKENES;

D O I：

10.1021/acs.joc.8b01143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium-catalyzed amide directed C-sp2-H activation of the quinazolinone scaffold has been demonstrated, leading to the selective mono- or dialkenylation in moderate to good yields to achieve medicinally important stilbene containing quinazolinones. The terminal allcyne is utilized as a coupling partner, which resulted in the selective trans-alkene formation. Electron-deficient phenylacetylenes facilitate alkenylation followed by tandem hydroamidation of the newly generated trans double bond to provide novel quinazolinone alkaloids related to the Luotonine class of natural products.

引用

页码：8906 / 8913

页数：8

共 48 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].

Ackermann, Lutz ;

Lygin, Alexander V. ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382

[3]

Ajani O., 2017, AM J DRUG DISCOVERY, V7, P1, DOI DOI 10.3923/AJDD.2017.1.24

[4]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

[5] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[6] Photophysical properties of push-pull 8-aryl-deoxyguanosine probes within duplex and G-quadruplex structures [J].

Blanchard, Darian J. M. ;

Fadock, Kaila L. ;

Sproviero, Michael ;

Deore, Prashant S. ;

Cservenyi, Thomas Z. ;

Manderville, Richard A. ;

Sharma, Purshotam ;

Wetmore, Stacey D. .

JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (14) :2915-2924

[7] Alkenylation of Arenes and Heteroarenes with Alkynes [J].

Boyarskiy, Vadim P. ;

Ryabukhin, Dmitry S. ;

Bokach, Nadezhda A. ;

Vasilyev, Aleksander V. .

CHEMICAL REVIEWS, 2016, 116 (10) :5894-5986

[8] Distal Weak Coordination of Acetamides in Ruthenium(II)-Catalyzed C-H Activation Processes [J].

Bu, Qingqing ;

Rogge, Torben ;

Kotek, Vladislav ;

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (03) :765-768

[9] Asymmetric hydrofunctionalization of minimally functionalized alkenes via earth abundant transition metal catalysis [J].

Chen, Jianhui ;

Lu, Zhan .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (02) :260-272

[10] RuCl3-Catalyzed Alkenylation of Aromatic C-H Bonds with Terminal Alkynes [J].

Cheng, Kai ;

Yao, Bangben ;

Zhao, Jinlong ;

Zhang, Yuhong .

ORGANIC LETTERS, 2008, 10 (22) :5309-5312

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