Palladium-catalyzed rearrangement/arylation of 2-allyloxypyridine leading to the synthesis of N-substituted 2-pyridones

被引：42

作者：

Itami, K ^{[1
]}

Yamazaki, D ^{[1
]}

Yoshida, J ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 12期

关键词：

D O I：

10.1021/ol0346234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Pd-catalyzed one-pot rearrangement/arylation of 2-allyloxypyridine is described. The catalyst/base combination of Pd[P(t-Bu)(3)](2)/Ag(2)CO(3) was found to be optimal for this one-pot rearrangement/arylation. The initial rearrangement of 2-allyloxypyridine was found to be catalyzed by both Pd(0) and Pd(II) complexes with different mechanisms.

引用

页码：2161 / 2164

页数：4

共 35 条

[21] ON THE PALLADIUM(II)-CATALYZED REARRANGEMENT OF ALLYL IMIDATES [J].

METZ, P ;

MUES, C ;

SCHOOP, A .

TETRAHEDRON, 1992, 48 (06) :1071-1080

[22] CLAISEN REARRANGEMENT OF ALLYLOXYPYRIDINES [J].

MOFFETT, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (10) :2885-&

[23] ALLYLIC AND PROPARGYLIC IMIDIC ESTERS IN ORGANIC-SYNTHESIS [J].

OVERMAN, LE .

ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (07) :218-224

[24] MERCURY(II)-CATALYZED AND PALLADIUM(II)-CATALYZED [3,3]-SIGMATROPIC REARRANGEMENTS [J].

OVERMAN, LE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :579-586

[25]

POTMESIL H, 1995, CAMPTOHECINS NEW ANT

[26]

Reddy ACS, 1996, TETRAHEDRON LETT, V37, P2829

[27] Preparation of N-alkylated pyridones via selective N-alkylation of 2-alkoxypyridines on solid phase [J].

Ruda, MC ;

Bergman, J ;

Wu, J .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (05) :530-535

[28]

SANDERSON PE, 1997, Patent No. 9701338

[29]

SATO T, 1995, SYNLETT, P845

[30] HOMOGENEOUS CATALYSIS - TRANSITION-METAL-CATALYZED CLAISEN REARRANGEMENTS [J].

SCHENCK, TG ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2058-2066

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