Palladium-Catalyzed [4+2] Cycloaddition of Vinyl Benzoxazinanones with 1,3-Indanedione: Approach to Spiro-Tetrahydroquinoline Scaffolds

被引：4

作者：

Wei, Qinglang ^{[1
]}

Tu, Liang ^{[1
]}

Li, Sen ^{[2
]}

Zheng, Yongsheng ^{[1
]}

Liu, Jikai ^{[1
]}

机构：

[1] South Cent Minzu Univ, Sch Pharmaceut Sci, Wuhan 430074, Peoples R China

[2] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414000, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 39期

基金：

中国国家自然科学基金;

关键词：

spiro-tetrahydroquinolines; 4+2] cycloaddition; vinyl benzoxazinanones; 1,3-indanediones; ASYMMETRIC CONSTRUCTION; DERIVATIVES; HYBRIDS; DESIGN;

D O I：

10.1002/ejoc.202300499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium catalyzed decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with 2-arylidene indan-1,3-dione has been established, which afford a series of bioactive spiro-tetrahydroquinolines (27 examples) in moderate to good yield (up to 87 %) with high diastereoselectivities. The synthetic utility of this reaction was demonstrated by gram-scale synthesis. Compounds synthesized by this method potently inhibited proliferation in a panel of cancer cell lines. Particularly, the most potent compounds 3 ae, 3 ah, 3 aj and 3 fa displayed selective inhibition of MDA-MB-231 breast carcinoma cells with IC50 values of 1.292, 0.6118, 0.6558, 1.656 and 2.215 & mu;M, respectively. A palladium catalyzed decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with 1,3-indanedione was developed, affording a series of biologically potential spiro-tetrahydroquinolines. Gram-scale synthesis and product elaboration demonstrated the utility of this method. The product demonstrated exhibited potency in inhibiting MDA-MB-231 cell line.+image

引用

页数：5

共 24 条

[21] Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2′-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines
Nawaz, Shah
Wei, Shiqiang
Huang, Yue
Wang, Wenyao
Qu, Jingping
Wang, Baomin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (32) : 6964 - 6968
[22] First Lewis acid catalyzed [4+2] cycloaddition reaction of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with chromones: a new entry to analogues of the puupehenone group of marine diterpenoids and kampanols
Kamble, Rajesh M.
Ramana, M. M. V.
MONATSHEFTE FUR CHEMIE, 2011, 142 (05): : 501 - 506
[23] Palladium-Catalyzed Decarboxylative Synthesis of 5H-Benzo[4,5][1,3]oxazino[2,3-a]isoindole-5,11(6aH)-Diones using 2-Phenyl-4H-Benzo[d][1,3]oxazin-4-Ones and α-Oxo Carboxylic Acids
Lalji, Ram Sunil Kumar
Kumar, Prashant
Gupta, Mohit
Parmar, Virinder S.
Singh, Brajendra K.
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 552 - 560
[24] Ultrasound-Assisted Expeditious Catalyst-Free Green Approach towards Diastereoselective Synthesis of Spiro[indoline-3,2′-pyrido[2,1-b][1,3]oxazine]-3′,4′-dicarboxylate Scaffolds
Mal, Kajal
Ray, Suman
Maity, Suvendu
Nurjamal, Khondekar
Ghosh, Prasanta
Brahmachari, Goutam
Mukhopadhyay, Chhanda
CHEMISTRYSELECT, 2021, 6 (06): : 1263 - 1270

← 1 2 3 →