Piperidinium Acetate-Catalyzed the Synthisis of 2,3-Disubstituted Chroman-4-one and 2,2-Disubstituted Benzofuran-3-one Derivatives

被引：5

作者：

Wang, Haifei ^{[1
]}

Zhou, Zhipeng ^{[1
]}

Hu, Shunqin ^{[1
]}

Wen, Pushan ^{[1
]}

Tao, Bin ^{[1
]}

Deng, Qifu ^{[1
]}

机构：

[1] Hunan Univ Technol, Sch Packaging & Mat Engn, Zhuzhou 412007, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 36卷 / 03期

关键词：

piperidinium acetate; cascade reaction; chroman-4-one; benzofuran-3-one; ENANTIOSELECTIVE SYNTHESIS; ORYZALEXIN-A; ADDITIONS;

D O I：

10.6023/cjoc201510014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A piperidinium acetate-catalyzed method was developed for the Knoevenagel and O-Micheal cascade reaction of o-hydroxyphenyl-beta-diketoes with different series of aldehydes. In the presence of piperidinium acetate, sixteen 2,3-disubstituted chroman-4-ones and nine 2,2-disubstituted benzofuran-3-ones were obtained in moderate to good yields, and the cascade reaction displayed better substrate adaptability. Moreover, the reaction has the following features: a convenient and simple path, mild reaction conditions and a cheap catalyst.

引用

页码：596 / 603

页数：8

共 27 条

[1] 3-HYDROXY-7-OXO-SANDARACOPIMARADIENE (ORYZALEXIN-A), A NEW PHYTOALEXIN ISOLATED FROM RICE BLAST LEAVES [J].

AKATSUKA, T ;

KODAMA, O ;

KATO, H ;

KONO, Y ;

TAKEUCHI, S .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (02) :445-447

[2] Catalytic enantioselective synthesis of flavanones and chromanones [J].

Biddle, Margaret M. ;

Lin, Michael ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3830-+

[3] Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes [J].

Brown, MK ;

Degrado, SJ ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5306-5310

[4] Topochemical photodimerization of (E)-3-benzylidene-4-chromanone derivatives from β-type structures directed by halogen groups [J].

Cheng, Xue-Ming ;

Huang, Zhi-Tang ;

Zheng, Qi-Yu .

TETRAHEDRON, 2011, 67 (47) :9093-9098

[5] New chiral rhodium(II) carboxylates and their use as catalysts in carbenoid transformations [J].

Ferris, L ;

Haigh, D ;

Moody, CJ .

TETRAHEDRON LETTERS, 1996, 37 (01) :107-110

[6] Convenient access to polysubstituted 1-indanones by Sc(OTf)3-catalyzed intramolecular Friedel-Crafts acylation of benzyl Meldrum's acid derivatives [J].

Fillion, E ;

Fishlock, D .

ORGANIC LETTERS, 2003, 5 (24) :4653-4656

[7] Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes [J].

Filloux, Claire M. ;

Lathrop, Stephen P. ;

Rovis, Tomislav .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) :20666-20671

[8] Studies on oxygen heterocycles part 2: Synthesis of 2-arylcoumaranones and 2-phenylbenzofuran [J].

Ghosh, S ;

Banerjee, I ;

Baul, S .

TETRAHEDRON, 1999, 55 (38) :11537-11546

[9] Rh(II)-binaphthol phosphate catalysts in the enantioselective intramolecular oxonium ylide formation-[3,2] sigmatropic rearrangement of α-diazo-β-ketoesters [J].

Hodgson, DM ;

Petroliagi, M .

TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :877-881

[10]

Hollingworth R.M., 1995, Reviews of Pesticide Toxicology, P277

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