Palladium-catalysed alkynylations of 2-pyrone (pyran-2-one) halides

被引：32

作者：

Fairlamb, IJS ^{[1
]}

Lu, FJ ^{[1
]}

Schmidt, JP ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

SYNTHESIS-STUTTGART | 2003年 / 16期

关键词：

palladium; Negishi reaction; Sonogashira reaction; 2-pyrones;

D O I：

10.1055/s-2003-42405

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-pyrone sub-unit is found in a large number of natural products possessing broad-spectrum biological activity. As such, efficient synthetic methods are required to enable facile access to substituted 2-pyrone derivatives. Important conditions for the Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone (3a) have been developed, and compared against Negishi's methodology. The best conditions for Sonogashira alkynylation was found to be the use of Pd/C with added Ph3P as the catalyst, in the presence of catalytic Cut, in a mixture of MeCN and Et3N at reflux. Using Negishi's standard conditions, terminal alkynylzinc reagents, generated in situ from terminal alkynes with LDA or n-BuLi and subsequent reaction with anhydrous ZnBr2, were reacted with 3a at room temperature using Pd(PPh3)(4) as the catalyst in THF.

引用

页码：2564 / 2570

页数：7

共 35 条

[1] 5-BROMO-2-PYRONE - AN EASILY PREPARED AMBIPHILIC DIENE AND A SYNTHETIC EQUIVALENT OF 2-PYRONE IN MILD, THERMAL, DIELS-ALDER CYCLOADDITIONS
AFARINKIA, K
POSNER, GH
[J]. TETRAHEDRON LETTERS, 1992, 33 (51) : 7839 - 7842
[2] DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES
AFARINKIA, K
VINADER, V
NELSON, TD
POSNER, GH
[J]. TETRAHEDRON, 1992, 48 (42) : 9111 - 9171
[3] N-OXIDES AND RELATED COMPOUNDS .56. PREPARATION OF NN'-LINKED BI(HETEROARYLS) FROM DEHYDROACETIC ACID AND 2,6-DIMETHYL-4-PYRONE
AFRIDI, AS
KATRITZKY, AR
RAMSDEN, CA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (12): : 1428 - 1436
[4] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions
Amatore, C
Jutand, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) : 314 - 321
[5] A novel route to 6-substituted and 5,6-disubstituted 2-pyrones
Bellina, F
Biagetti, M
Carpita, A
Rossi, R
[J]. TETRAHEDRON LETTERS, 2001, 42 (15) : 2859 - 2863
[6] Fast synthesis of aryl triflates with controlled microwave heating
Bengtson, A
Hallberg, A
Larhed, M
[J]. ORGANIC LETTERS, 2002, 4 (07) : 1231 - 1233
[7] BULOCK JD, 1960, J CHEM SOC, V502
[8] 3-aryl and 5-aryl-4-methoxy-6-methyl-2H-pyran-2-ones by Suzuki cross-coupling reactions of 3- and 5-halogeno-4-methoxy-6-methyl-2H-pyran-2-ones
Cerezo, S
Moreno-Mañas, M
Pleixats, R
[J]. TETRAHEDRON, 1998, 54 (27) : 7813 - 7818
[9] 4-AMINO-6-METHYL-2H-PYRAN-2-ONE - PREPARATION AND REACTIONS WITH AROMATIC-ALDEHYDES
CERVERA, M
MORENOMANAS, M
PLEIXATS, R
[J]. TETRAHEDRON, 1990, 46 (23) : 7885 - 7892
[10] One-pot stereoselective synthesis of tricyclic bislactones from 2-pyrones and 2-methoxyfuran
Chen, CH
Liao, CC
[J]. ORGANIC LETTERS, 2000, 2 (14) : 2049 - 2052

← 1 2 3 4 →