Ru(ii)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines

被引：16
作者：
Yang, Yurong [1 ,2 ,3 ]
Zhang, Kaixin [1 ,2 ,3 ]
Yang, Jian [1 ,2 ,3 ]
Zhu, Guoxun [1 ,2 ,3 ]
Chen, Weijie [1 ,2 ,3 ]
Zhang, Chao [1 ,2 ,3 ]
Zhou, Zhi [1 ,2 ,3 ]
Yi, Wei [1 ,2 ,3 ]
机构：
[1] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China
[2] Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China
[3] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 76期
关键词：
C-H ACTIVATION; PROPARGYL ALCOHOLS; FUNCTIONALIZATION; ACCESS; DERIVATIVES; BENZAMIDES; COUPLINGS; KETONES;
D O I：
10.1039/d0cc04041j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Ru(ii)-catalyzed tunable [5+1]/[5+2] annulation ofN-benzo[d]imidazole indolines with propargyl carbonates has been realized for the divergent synthesis of ring-fused quinazolines and 1,3-benzodiazepines bearing various functional groups. These transformations represent an efficient and practical strategy in constructing complex heterocyclesviadiversified C-H functionalization. A distinctive acidity-controlled reaction manner has been clarified to account for the chemoselectivity.
引用
收藏
页码：11315 / 11318
页数：4
相关论文
共 47 条
[1]   Rhodium(III)-catalyzed chemoselective C-H functionalization of benzamides with methyleneoxetanones controlled by the solvent [J].
Bian, Mengyao ;
Ma, Kuangshun ;
Mawjuda, Hamdulla ;
Yu, Xiyong ;
Li, Xingwei ;
Gao, Hui ;
Zhou, Zhi ;
Yi, Wei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) :6114-6118
[2]   Biologically active carbazole derivatives: focus on oxazinocarbazoles and related compounds [J].
Bouaziz, Zouhair ;
Issa, Samar ;
Gentili, Jacques ;
Gratz, Andreas ;
Bollacke, Andre ;
Kassack, Matthias ;
Jose, Joachim ;
Herfindal, Lars ;
Gausdal, Gro ;
Doskeland, Stein Ove ;
Mullie, Catherine ;
Sonnet, Pascal ;
Desgrouas, Camille ;
Taudon, Nicolas ;
Valdameri, Glaucio ;
Di Pietro, Attilio ;
Baitiche, Milad ;
Le Borgne, Marc .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2015, 30 (02) :180-188
[3]   Rh(III)-catalyzed [5+1] oxidative cycloaddition of arylguanidines with alkynes: a novel access to C4-disubstituted 1,4-dihydroquinazolin-2-amines [J].
Cajaraville, Ana ;
Suarez, Jaime ;
Lopez, Susana ;
Varela, Jesus A. ;
Saa, Carlos .
CHEMICAL COMMUNICATIONS, 2015, 51 (82) :15157-15160
[4]   Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation [J].
Chen, Zhen ;
Rong, Meng-Yu ;
Nie, Jing ;
Zhu, Xue-Feng ;
Shi, Bing-Feng ;
Ma, Jun-An .
CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) :4921-4942
[5]   Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization [J].
Diesel, Johannes ;
Cramer, Nicolai .
ACS CATALYSIS, 2019, 9 (10) :9164-9177
[6]   3d Transition Metals for C-H Activation [J].
Gandeepan, Parthasarathy ;
Mueller, Thomas ;
Zell, Daniel ;
Cera, Gianpiero ;
Warratz, Svenja ;
Ackermann, Lutz .
CHEMICAL REVIEWS, 2019, 119 (04) :2192-2452
[7]   Catalyst-Controlled [3+2] and [4+2] Annulations of Oximes with Propargyl Alcohols: Divergent Access to Indenamines and Isoquinolines [J].
Gong, Wanchun ;
Zhou, Zhi ;
Shi, Jingjing ;
Wu, Bo ;
Huang, Biyun ;
Yi, Wei .
ORGANIC LETTERS, 2018, 20 (01) :182-185
[8]   Palladium-Catalyzed C(sp3)-H Bond Functionalization of Aliphatic Amines [J].
He, Chuan ;
Whitehurst, William G. ;
Gaunt, Matthew J. .
CHEM, 2019, 5 (05) :1031-1058
[9]   Synthesis of Heterocycles by Using Propargyl Compounds as Versatile Synthons [J].
Hua, Ruimao ;
Nizami, Tauqir A. .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2018, 15 (03) :198-207
[10]   Site-Selective C-H Functionalization via Synergistic Use of Electrochemistry and Transition Metal Catalysis [J].
Jiao, Ke-Jin ;
Xing, Yi-Kang ;
Yang, Qi-Liang ;
Qiu, Hui ;
Mei, Tian-Sheng .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (02) :300-310
12345