Arylation of allylphosphonates and application to the preparation of phosphonomethyl-coumarin, -quinolinone and -benzoxepinone skeletons

被引：9

作者：

Abdelli, Abderrahmen ^{[1
,2
]}

Gaucher, Anne ^{[1
]}

Efrit, Mohamed Lotfi ^{[2
]}

M'rabet, Hedi ^{[2
]}

Prim, Damien ^{[1
]}

机构：

[1] Univ Versailles St Quentin En Yvelines, Inst Lavoisier Versailles, UMR CNRS 8180, F-78035 Versailles, France

[2] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl, Tunis 2092, Tunisia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 13期

关键词：

Allylphosphonate; Coumarin; Quinolinone; Benzoxepinone; EFFICIENT SYNTHESIS; PHOSPHONATES; MILD;

D O I：

10.1016/j.tetlet.2015.02.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and selective synthesis of Z-(het)arylallylphosphonates is described. The versatile Pd-assisted process also allowed polyarylation sequences leading to star-shaped and binaphthyl derivatives. The methodology could be extended to the preparation of new phosphonomethyl-coumarin, -quinolinone, and -benzoxepinone architectures in high yields. (C) 2015 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1679 / 1681

页数：3

相关论文

共 19 条

[1] γ-Alkylsulfide phosphonates through the thia-Michael strategy [J].

Abdelli, Abderrahmen ;

M'rabet, Hedi ;

Efrit, Mohamed Lotfi ;

Gaucher, Anne ;

Prim, Damien .

JOURNAL OF SULFUR CHEMISTRY, 2014, 35 (06) :674-682

[2] Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach [J].

Boeck, Florian ;

Blazejak, Max ;

Anneser, Markus R. ;

Hintermann, Lukas .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1630-1636

[3] SIMPLE AND ADVANTAGENEOUS STEREOSELECTIVE SYNTHESIS OF (Z)-ALLYL PHOSPHONATES STARTING FROM BAYLIS-HILLMAN ADDUCTS [J].

Das, Biswanath ;

Bhunia, Nisith ;

Damodar, Kongara .

SYNTHETIC COMMUNICATIONS, 2012, 42 (17) :2479-2489

[4] Asymmetric Michael reaction:: novel efficient access to chiral β-ketophosphonates [J].

Delarue-Cochin, Sandrine ;

Pan, Jian-Jung ;

Dauteloup, Aurelie ;

Hendra, Frederic ;

Angoh, Roger Gagali ;

Joseph, Delphine ;

Stephens, Philip J. ;

Cave, Christian .

TETRAHEDRON-ASYMMETRY, 2007, 18 (05) :685-691

[5]

Demik N. N., 1994, J ORG CHEM, V30, P935

[6] Nonpeptidic vinyl and allyl phosphonates as falcipain-2 inhibitors [J].

Ettari, Roberta ;

Nizi, Emanuela ;

Di Francesco, Maria Emilia ;

Micale, Nicola ;

Grasso, Silvana ;

Zappala, Maria ;

Vicik, Radim ;

Schirmeister, Tanja .

CHEMMEDCHEM, 2008, 3 (07) :1030-1033

[7]

JANECKI T, 1989, SYNTHESIS-STUTTGART, P506

[8] HPLC-SPE-NMR Identification of a Novel Metabolite Containing the Benzo[c]oxepin Skeleton from the Endophytic Fungus Pestalotiopsis virgatula Culture [J].

Kesting, Julie R. ;

Staerk, Dan ;

Tejesvi, Mysore V. ;

Kini, Kukkundoor R. ;

Prakash, Harishchandra S. ;

Jaroszewski, Jerzy W. .

PLANTA MEDICA, 2009, 75 (10) :1104-1106

[9] An Efficient Synthesis of Phospha-Morita-Baylis-Hillman Adducts via Michaelis-Arbuzov Reaction of the DABCO Salt of Morita-Baylis-Hillman Bromide [J].

Kim, Sung Hwan ;

Kim, Se Hee ;

Lee, Hyun Seung ;

Kim, Jae Nyoung .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (01) :133-138

[10] Pd-Catalyzed Oxidative Arylation of Cinnamylphosphonates: An Efficient Synthesis of (Z)-Alkenylphosphonates [J].

Lee, Hyun Seung ;

Lim, Cheol Hee ;

Lee, Hyun Ju ;

Kim, Jae Nyoung .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (11) :3817-3822