Efficient synthesis of tetrahydronaphthalene- or isochroman-fused spirooxindoles using tandem reactions

被引:23
作者
Wang, Biao [1 ]
Leng, Hai-Jun [2 ]
Yang, Xue-Yuan [1 ]
Han, Bo [1 ]
Rao, Chao-Long [2 ]
Liu, Li [2 ]
Peng, Cheng [1 ,2 ]
Huang, Wei [1 ]
机构
[1] Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Peoples R China
[2] Chengdu Univ Tradit Chinese Med, Sch Pharm, Minist Educ, Key Lab Standardizat Chinese Med, Chengdu 611137, Peoples R China
基金
中国国家自然科学基金;
关键词
ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; NATURAL-PRODUCTS; DRUG-LIKE; DERIVATIVES; CYCLIZATION; MICHAEL; SCAFFOLDS; OXINDOLES;
D O I
10.1039/c5ra15735h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The flexible and simple cascade reaction involving a Michael-aldol or vinylogous Henry-acetalization relay is described. We have used the cascade reaction to assemble functionalized tetrahydronaphthalene- or isochroman-fused spirooxindoles and other drug-like spirocyclic scaffolds. The mild reaction conditions, short reaction times, and high tolerance for various functional groups make this method attractive for constructing pharmacologically interesting architectures.
引用
收藏
页码:88272 / 88276
页数:5
相关论文
共 59 条
[1]   Antimicrobial activities of some tetrahydronaphthalene-benzimidazole derivatives [J].
Ates-Alagoz, Zeynep ;
Yildiz, Sulhiye ;
Buyukbingo, Erdem .
CHEMOTHERAPY, 2007, 53 (02) :110-113
[2]   Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates [J].
Bai, Renren ;
Huang, Xiaojing ;
Yang, Xue ;
Hong, Wen ;
Tang, Yiqun ;
Yao, Hequan ;
Jiang, Jieyun ;
Liu, Jie ;
Shen, Mingqin ;
Wu, Xiaoming ;
Xu, Jinyi .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (09) :2495-2502
[3]   Novel nitric oxide-releasing isochroman-4-one derivatives: Synthesis and evaluation of antihypertensive activity [J].
Bai, Renren ;
Yang, Xue ;
Zhu, Yao ;
Zhou, Zhiwen ;
Xie, Weijia ;
Yao, Hequan ;
Jiang, Jieyun ;
Liu, Jie ;
Shen, Mingqin ;
Wu, Xiaoming ;
Xu, Jinyi .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (23) :6848-6855
[4]   Strategies for the enantioselective synthesis of spirooxindoles [J].
Ball-Jones, Nicolas R. ;
Badillo, Joseph J. ;
Franz, Annaliese K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181
[5]   Dissociated nonsteroidal glucocorticoid receptor modulators; Discovery of the agonist trigger in a tetrahydronaphthalene-benzoxazine series [J].
Barker, Mike ;
Clackers, Margaret ;
Copley, Royston ;
Demaine, Derek A. ;
Humphreys, Davina ;
Inglis, Graham G. A. ;
Johnston, Michael J. ;
Jones, Haydn T. ;
Haase, Michael V. ;
House, David ;
Loiseau, Richard ;
Nisbet, Lesley ;
Pacquet, Francois ;
Skone, Philip A. ;
Shanahan, Stephen E. ;
Tape, Dan ;
Vinader, Victoria M. ;
Washington, Melanie ;
Uings, Iain ;
Upton, Richard ;
Mclay, Iain M. ;
Macdonald, Simon J. F. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (14) :4216-4231
[6]   Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies [J].
Cheng, Daojuan ;
Ishihara, Yoshihiro ;
Tan, Bin ;
Barbas, Carlos F., III .
ACS CATALYSIS, 2014, 4 (03) :743-762
[7]   Enantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems [J].
Das, Jaya Prakash ;
Marek, Ilan .
CHEMICAL COMMUNICATIONS, 2011, 47 (16) :4593-4623
[8]   Asymmetric Organocatalytic Benzylation of α,β-Unsaturated Aldehydes with Toluenes [J].
Dell'Amico, Luca ;
Companyo, Xavier ;
Naicker, Tricia ;
Brauer, Thomas M. ;
Jorgensen, Karl Anker .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) :5262-5265
[9]   One-pot synthesis of isothiachromene, isochromene, isoquinoline and tetrahydronaphthalene derivatives [J].
El-Sayed, AM ;
Abdel-Ghany, H .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (05) :1233-1240
[10]   Substitution and cyclization reactions involving the quasi-antiaromatic 2H-indol-2-one ring system [J].
England, Dylan B. ;
Merey, Gokce ;
Padwa, Albert .
ORGANIC LETTERS, 2007, 9 (19) :3805-3807