Synthesis of Oxo-Bridged Dibenzoazocines through Ruthenium-Catalyzed [4+3]-Cycloannulation of Aza-ortho-quinone Methides with Carbonyl Ylides

被引：3

作者：

Jia, Pengfei ^{[1
,2
,3
]}

Lin, Zhiqian ^{[1
,2
,3
]}

Yan, Shenmeng ^{[1
,2
,3
]}

Liang, Jiao ^{[1
,2
,3
]}

Luo, Cankun ^{[1
,2
,3
]}

Lai, Ruizhi ^{[1
,2
,3
]}

Hai, Li ^{[1
,2
,3
]}

Yang, Zhongzhen ^{[1
,2
,3
]}

Wu, Yong ^{[1
,2
,3
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China

[2] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Sichuan Engn Lab Plant Sourced Drug, Chengdu 610041, Sichuan, Peoples R China

[3] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 27期

关键词：

DIELS-ALDER REACTIONS; PHOTOASSISTED ACCESS; 1,3-DIPOLAR CYCLOADDITION; CYCLIZATION; ENOLDIAZOACETAMIDES; ANNULATION; IMINES;

D O I：

10.1021/acs.orglett.3c01885

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxo-bridgeddibenzoazocines are furnished within a single syntheticstep at room temperature via ruthenium-catalyzed [4 + 3]-cycloannulationof aza-ortho-quinone methides with carbonyl ylides.Exclusive diastereoselectivity, excellent yield, mild reaction conditions,and broad substrate scope are distinguishing features of this protocol.The product could be prepared on a gram scale and could be furtherfunctionalized into diverse substituted dihydroisobenzofuran derivativesand a dibenzoazocine scaffold.

引用

页码：5134 / 5139

页数：6

共 6 条

[1] Cooperative Catalysis for the Highly Diastereo- and Enantioselective [4+3]-Cycloannulation of ortho-Quinone Methides and Carbonyl Ylides
Suneja, Arun
Loui, Henning Jakob
Schneider, Christoph
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5536 - 5540
[2] Construction of Oxo-Bridged Diazocines via Rhodium-Catalyzed (4+3) Cycloaddition of Carbonyl Ylides with Azoalkenes
Pang, Qiwen
Zhou, Jin
Wu, Yuling
Zhou, Wu-Jingyun
Zuo, Wei-Fang
Zhan, Gu
Han, Bo
ORGANIC LETTERS, 2022, 24 (06) : 1362 - 1366
[3] A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triaze-pines
Wang, Xinyue
Li, Zefei
Feng, Chang
Zhen, Qi
Guo, Mingzhang
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SYNLETT, 2021, 32 (20) : 2090 - 2096
[4] Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides
Carceller-Ferrer, Laura
Rodriguez-Arias, Carlos
Montesinos-Magraner, Marc
Sanz-Marco, Amparo
Hostalet-Romero, Judit
Blay, Gonzalo
Pedro, Jose R.
Vila, Carlos
HELVETICA CHIMICA ACTA, 2024, 107 (04)
[5] Synthesis of biologically active [1,5]diazocino[2,1-b]quinazolinones through [4+4] cycloaddition of 2-alkynyl quinazolinones with aza-ortho-quinone methides
Pang, Li
Fang, Shu-Jun
Zou, Pei-Sen
Wang, Wang
Su, Jun-Cheng
Liu, Xiao-Qing
Pan, Cheng-Xue
Mo, Dong-Liang
Su, Gui-Fa
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (07): : 1780 - 1787
[6] Lewis Base-Catalyzed [4+3] Annulation of ortho-Quinone Methides and MBH Carbonates: Synthesis of Functionalized Benzo[b]oxepines Bearing Oxindole Scaffolds
Du, Ji-Yuan
Ma, Yan-Hua
Meng, Fan-Xiao
Zhang, Rui-Rui
Wang, Ruo-Nan
Shi, Hong-Liang
Wang, Qi
Fan, Ya-Xin
Huang, Hong-Li
Cui, Ji-Chun
Ma, Chun-Lin
ORGANIC LETTERS, 2019, 21 (02) : 465 - 468

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