Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction

被引：153

作者：

Awuah, Emelia ^{[1
]}

Capretta, Alfredo ^{[1
]}

机构：

[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CATALYZED CARBONYLATION; BIOLOGICAL EVALUATION; ARYL CHLORIDES; INHIBITORS; IODIDES; AMINOCARBONYLATION;

D O I：

10.1021/ol901043q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane are shown to be effective catalytic systems facilitating the sequential application of a microwave-assisted Sonogashira and carbonylative annulation reaction for the preparation of substituted flavones.

引用

页码：3210 / 3213

页数：4

共 27 条

[1] Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].

Adjabeng, G ;

Brenstrum, T ;

Frampton, CS ;

Robertson, AJ ;

Hillhouse, J ;

McNulty, J ;

Capretta, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5082-5086

[2]

Andersen O. M., 2006, FLAVONOIDS CHEM BIOC

[3] Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones [J].

Baker, W .

JOURNAL OF THE CHEMICAL SOCIETY, 1933, :1381-1389

[4] Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].

Barnard, Christopher F. J. .

ORGANOMETALLICS, 2008, 27 (21) :5402-5422

[5] Synthetic chalcones, flavanones, and flavones as antitumoral agents:: Biological evaluation and structure-activity relationships [J].

Cabrera, Mauricio ;

Simoens, Macarena ;

Falchi, Gabriela ;

Lavaggi, M. Laura ;

Piro, Oscar E. ;

Castellano, Eduardo E. ;

Vidal, Anabel ;

Azqueta, Amaia ;

Monge, Antonio ;

de Cerain, Adela Lopez ;

Sagrera, Gabriel ;

Scoane, Gustavo ;

Cerecetto, Hugo ;

Gonzalez, Mercedes .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) :3356-3367

[6] PREPARATIVE AND REGIOCHEMICAL ASPECTS OF THE PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF 2-HYDROXYARYL IODIDES WITH ETHYNYLARENES [J].

CIATTINI, PG ;

MORERA, E ;

ORTAR, G ;

ROSSI, SS .

TETRAHEDRON, 1991, 47 (32) :6449-6456

[7] Novel CFTR chloride channel activators identified by screening of combinatorial libraries based on flavone and benzoquinolizinium lead compounds [J].

Galietta, LJV ;

Springsteel, MF ;

Eda, M ;

Niedzinski, EJ ;

By, K ;

Haddadin, MJ ;

Kurth, MJ ;

Nantz, MH ;

Verkman, AS .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (23) :19723-19728

[8] Enantiopure tetrahydro-β-carbolines via Pictet-Spengler reactions with N-sulfinyl tryptamines [J].

Gremmen, C ;

Willemse, B ;

Wanner, MJ ;

Koomen, GJ .

ORGANIC LETTERS, 2000, 2 (13) :1955-1958

[9] Selective benzopyranone and pyrimido[2,1-α]isoquinolin-4-one inhibitors of DNA-dependent protein kinase:: Synthesis, structure-activity studies, and radiosensitization of a human tumor cell line in vitro [J].

Griffin, RJ ;

Fontana, G ;

Golding, BT ;

Guiard, S ;

Hardcastle, IR ;

Leahy, JJJ ;

Martin, N ;

Richardson, C ;

Rigoreau, L ;

Stockley, M ;

Smith, GCM .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :569-585

[10] Flavonolignan and flavone inhibitors of a Staphylococcus aureus multidrug resistance pump:: Structure-activity relationships [J].

Guz, NR ;

Stermitz, FR ;

Johnson, JB ;

Beeson, TD ;

Willen, S ;

Hsiang, JF ;

Lewis, K .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (02) :261-268

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