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

被引：14

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

页码：11315 / 11318

页数：4

共 47 条

[1] Rhodium(III)-catalyzed chemoselective C-H functionalization of benzamides with methyleneoxetanones controlled by the solvent
Bian, Mengyao
Ma, Kuangshun
Mawjuda, Hamdulla
Yu, Xiyong
Li, Xingwei
Gao, Hui
Zhou, Zhi
Yi, Wei
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (25) : 6114 - 6118
[2] Biologically active carbazole derivatives: focus on oxazinocarbazoles and related compounds
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
[J]. 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
Cajaraville, Ana
Suarez, Jaime
Lopez, Susana
Varela, Jesus A.
Saa, Carlos
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (82) : 15157 - 15160
[4] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
Chen, Zhen
Rong, Meng-Yu
Nie, Jing
Zhu, Xue-Feng
Shi, Bing-Feng
Ma, Jun-An
[J]. CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942
[5] Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization
Diesel, Johannes
Cramer, Nicolai
[J]. ACS CATALYSIS, 2019, 9 (10) : 9164 - 9177
[6] 3d Transition Metals for C-H Activation
Gandeepan, Parthasarathy
Mueller, Thomas
Zell, Daniel
Cera, Gianpiero
Warratz, Svenja
Ackermann, Lutz
[J]. 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
Gong, Wanchun
Zhou, Zhi
Shi, Jingjing
Wu, Bo
Huang, Biyun
Yi, Wei
[J]. ORGANIC LETTERS, 2018, 20 (01) : 182 - 185
[8] Palladium-Catalyzed C(sp3)-H Bond Functionalization of Aliphatic Amines
He, Chuan
Whitehurst, William G.
Gaunt, Matthew J.
[J]. CHEM, 2019, 5 (05): : 1031 - 1058
[9] Synthesis of Heterocycles by Using Propargyl Compounds as Versatile Synthons
Hua, Ruimao
Nizami, Tauqir A.
[J]. 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
Jiao, Ke-Jin
Xing, Yi-Kang
Yang, Qi-Liang
Qiu, Hui
Mei, Tian-Sheng
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (02) : 300 - 310

← 1 2 3 4 5 →