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 17 条

[1] Synthesis of 1,3-Benzodiazepines through [5+2] Annulation of N-Aryl Amidines with Propargylic Esters
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ORGANIC LETTERS, 2020, 22 (24) : 9506 - 9512
[2] Combinatorial synthesis of substituted pyrazolo-fused quinazolines by the Rh(iii)-catalyzed [5+1] annulation of phenyl-1H-pyrazol-5-amine with alkynoates and alkynamides
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[3] Rhodium-Catalyzed (5+2) and (5+1) Cycloadditions Using 1,4-Enynes as Five-Carbon Building Blocks
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[4] Rh(III)-Catalyzed [5+2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT
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[6] Platinum-catalyzed 1,3-acyloxy migration/[1,5]-hydride transfer/cycloaddition sequence: synthesis of ring-fused tetrahydroquinolines
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[7] Iron-Catalyzed, Iminyl Radical-Triggered Cascade 1,5-Hydrogen Atom Transfer/(5+2) or (5+1) Annulation: Oxime as a Five-Atom Assembling Unit
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[9] Nickel(II)-Catalyzed [5+1] Annulation of 2-Carbonyl-1-propargylindoles with Hydroxylamine To Synthesize Pyrazino[1,2-a]indole-2-oxides in Water
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[10] A substrate-controlled Ru(ii)-catalyzed C-H activation/[5+2] annulation cascade and unusual acyl migration to synthesize diverse indoline scaffolds
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