Efficient synthesis of dihydronaphthalenes via cerium-catalyzed annulation of 1-alkoxy substituted 1H-isochromenes with cinnamic acids

被引：0

作者：

Guo, Meng ^{[1
,2
,3
]}

Zhang, Xuetao ^{[1
,2
,3
]}

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

Chen, Yanmei ^{[1
,2
,3
]}

Zhang, Jun ^{[1
,2
,3
]}

Liu, Zhiqing ^{[1
,2
,3
]}

Wang, Chang-Yun ^{[1
,2
,3
,4
]}

Wang, Pingyuan ^{[1
,2
,3
]}

机构：

[1] Ocean Univ China, Key Lab Evolut & Marine Biodivers, Minist Educ, Qingdao 266003, Peoples R China

[2] Ocean Univ China, Inst Evolut & Marine Biodivers, Qingdao 266003, Peoples R China

[3] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao 266003, Peoples R China

[4] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2025年 / 23卷 / 07期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ETHERS; 1,2-DIHYDRONAPHTHALENES; BENZANNULATION; DERIVATIVES; DISCOVERY; ACETALS; ROOTS;

D O I：

10.1039/d4ob01895h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dihydronaphthalenes play a crucial role in bioactive natural products and new drug discovery, and efficient and economic strategies to build them are needed. Herein, we disclose a highly efficient method to prepare dihydronaphthalenes via a cerium-catalyzed cycloaddition of 1H-isochromenes with cinnamic acids. This newly developed method not only features a broad and low-cost substrate scope and mild conditions but also exhibits very high functional group tolerance, including hydroxyl, borate ester and ester group substituents. In addition, the practicality of this general strategy is demonstrated by gram-scale reactions and derivatizations, and all of the reactions proceed smoothly to afford the desired compounds in excellent yields.

引用

页码：1617 / 1621

页数：5

共 50 条

[41] Synthesis of Highly Substituted Pyrrole and Dihydro-1H-Pyrrole Containing Barbituric Acids via Catalyst-Free One-Pot Four-Component Reactions
Ghandi, Mehdi
Jourablou, Ali
Abbasi, Alireza
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3108 - 3119
[42] Palladium-Catalyzed [4+2] Annulation of Aryl and Alkenyl Carboxamides with 1,3-Dienes via C-H Functionalization: Synthesis of 3,4-Dihydroisoquinolones and 5,6-Dihydropyridinones
Sun, Manman
Li, Jinshan
Chen, Weida
Wu, Haijian
Yang, Jianguo
Wang, Zhiming
SYNTHESIS-STUTTGART, 2020, 52 (08): : 1253 - 1265
[43] Combining Isocyanides with Carbon Dioxide in Palladium-Catalyzed Heterocycle Synthesis: N3-Substituted Quinazoline-2,4(1H,3H)-diones via a Three-Component Reaction
Mampuys, Pieter
Neumann, Helfried
Sergeyev, Sergey
Orru, Romano V. A.
Jiao, Haijun
Spannenberg, Anke
Maes, Bert U. W.
Beller, Matthias
ACS CATALYSIS, 2017, 7 (08): : 5549 - 5556
[44] A one-pot synthesis of 2,3-dihydrobenzofurans, benzofuran-2(3H)-ones, and indoles via a [4+1] annulation reaction of ortho-substituted para-quinone methides and bromonitromethane
Savekar, Amol T.
Karande, Vishal B.
Hingane, Dattatray G.
Waghmode, Suresh B.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (45) : 8945 - 8950
[45] Efficient and Direct Route to 5-Iodo-4 H -Quinoxalines via Copper-Catalyzed Double C-N Arylations of 1,2,3-Triiodoarenes: Potential Application towards 5-Substituted 4 H -Quinoxalines
Al-Zoubi, Raed M.
Al-Jammal, Walid K.
Shkoor, Mohanad
Bani-Yaseen, Abdulilah D.
Ferguson, Michael J.
SYNTHESIS-STUTTGART, 2024, 56 (23): : 3680 - 3686
[46] Mild Cu(OAc)2•H2O-catalyzed synthesis of multi-substituted 1,2,4-triazoles from amidines with nitriles via a N-N/C-N coupling
Wang, Fei
You, Qing
Wu, Chaoting
Min, Dewen
Shi, Tianchao
Kong, Yuting
Zhang, Wu
RSC ADVANCES, 2015, 5 (96) : 78422 - 78426
[47] Efficient three-component one-pot synthesis of fully substituted pyridin-2(1H)-ones via tandem Knoevenagel condensation-ring-opening of cyclopropane-intramolecular cyclization
Liang, Fushun
Cheng, Xin
Liu, Jing
Liu, Qun
CHEMICAL COMMUNICATIONS, 2009, (24) : 3636 - 3638
[48] MCM-41-SO3H-catalyzed synthesis of highly substituted 3-amino-imidazo[1,2-a]pyridines or pyrazines via the Groebke-Blackburn-Bienayme multicomponent reaction under grinding conditions at ambient temperature
Naeimabadi, M.
Javanshir, Sh.
Maleki, A.
Dekamin, M. G.
SCIENTIA IRANICA, 2016, 23 (06) : 2724 - 2734
[49] An efficient p-TSA catalyzed synthesis of some new substituted- (5-hydroxy-3-phenylisoxazol-4-yl)-1,3-dimethyl-1 H-chromeno[2,3-d] pyrimidine-2,4(3H,5H)-dione/3,3-dimethyl-2H-xanthen-1(9H)-one scaffolds and evaluation of their pharmacological and computational investigations
Sukanya, S. H.
Venkatesh, Talavara
Rao, S. J. Aditya
Pandith, Anup
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1267
[50] Trinuclear cis-[MoVIO2] complexes catalyzed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one based biomolecules via one-pot-three-components Biginelli reaction under solvent-free condition
Maurya, Mannar R.
Singh, Devesh
Tomar, Reshu
Gupta, Puneet
INORGANICA CHIMICA ACTA, 2022, 532

← 1 2 3 4 5 →