Radical C-H Bond Oxidation Initiated Intramolecular Cyclization of Glycine Esters: Construction of Dihydroquinoline Skeletons

被引：5

作者：

Chen, Qian ^{[1
]}

Zhang, Shuwei ^{[1
]}

Zhang, Ting ^{[1
]}

He, Kaixuan ^{[1
]}

Yuan, Yu ^{[1
]}

Jia, Xiaodong ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 8卷 / 01期

基金：

中国国家自然科学基金;

关键词：

sp(3) C-H activation; radical cation salt; aerobic oxidation; cyclization; dihydroquinoline; DERIVATIVES; FUNCTIONALIZATION; ANALOGS; PODOPHYLLOTOXIN; ACTIVATION; QUINOLINE;

D O I：

10.1002/ajoc.201800596

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient construction of dihydroquinoline derivatives was realized through radical cation salt-initiated C-H bond oxidation of unsaturated glycine esters. In the presence of dioxygen, the sp(3) C-H bond adjacent to nitrogen was oxidized, followed by cascade cyclization, affording the desired dihydroquinoline products. The mechanistic investigation revealed that a radical intermediate was involved in this reaction.

引用

页码：115 / 118

页数：4

共 57 条

[1] Enantioselective Organocatalytic Partial Transfer Hydrogenation of Lactone-Fused Quinolines
Aillerie, Alexandre
de Talance, Vincent Lemau
Moncomble, Aurelien
Bousquet, Till
Pelinski, Lydie
[J]. ORGANIC LETTERS, 2014, 16 (11) : 2982 - 2985
[2] Heteroatom- and carbon-linked biphenyl analogs of brequinar as immunosuppressive agents
Batt, DG
Petraitis, JJ
Sherk, SR
Copeland, RA
Dowling, RL
Taylor, TL
Jones, EA
Magolda, RL
Jaffee, BD
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (13) : 1745 - 1750
[3] Synthesis of Highly Substituted Arenes via Cyclohexadiene-Alkene C-H Cross Coupling and Aromatization
Bhunia, Anup
Studer, Armido
[J]. ACS CATALYSIS, 2018, 8 (02): : 1213 - 1217
[4] Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes
Cabrera, Pablo J.
Lee, Melissa
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (16) : 5599 - 5606
[5] Catalytic one-pot microwave assisted synthesis of 4-azapodophyllotoxin derivatives and rational design of experiment
Chang, Peng
Aillerie, Alexandre
Kosmala, Marion
Pellegrini, Sylvain
Bousquet, Till
Bigan, Muriel
Pelinski, Lydie
[J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (11) : 8236 - 8239
[6] Complementary Strategies for Directed C(sp3)-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer
Chu, John C. K.
Rovis, Tomislav
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (01) : 62 - 101
[7] Nonsteroidal selective glucocorticoid modulators: The effect of C-5 alkyl substitution on the transcriptional activation/repression profile of 2,5-dihydro-10-methoxy-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolines
Elmore, SW
Coghlan, MJ
Anderson, DD
Pratt, JK
Green, BE
Wang, AX
Stashko, MA
Lin, CW
Tyree, CM
Miner, JN
Jacobson, PB
Wilcox, DM
Lane, BC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (25) : 4481 - 4491
[8] FELICIANO AS, 1989, PHYTOCHEMISTRY, V28, P659
[9] Insecticidal heterolignans-Tubuline polymerization inhibitors with activity against chewing pests
Frackenpohl, Jens
Adelt, Isabelle
Antonicek, Horst
Arnold, Christian
Behrmann, Patricia
Blaha, Nicole
Boehmer, Jutta
Gutbrod, Oliver
Hanke, Roman
Hohmann, Sabine
van Houtdreve, Marc
Loesel, Peter
Malsam, Olga
Melchers, Martin
Neufert, Valentina
Peschel, Elisabeth
Reckmann, Udo
Schenke, Thomas
Thiesen, Hans-Peter
Velten, Robert
Vogelsang, Kathrin
Weiss, Hans-Christoph
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (12) : 4160 - 4184
[10] Cobalt(II)-Catalyzed Electrooxidative C-H Amination of Arenes with Alkylamines
Gao, Xinlong
Wang, Pan
Zeng, Li
Tang, Shan
Lei, Aiwen
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (12) : 4195 - 4199

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