ACYLIMINIUM IONS DERIVED FROM THE REARRANGEMENT OF BISCHLER-NAPIERALSKI CYCLIZATION PRODUCTS

被引：23

作者：

HEANEY, H

SHUHAIBAR, KF

机构：

[1] Department of Chemistry, The University of Technology, Loughborough

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(00)77023-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of pyrophosphoryl chloride with amides derived from arylethylamines and related compounds with 2-methoxycarbonylbenzoyl chloride give the expected Bischler-Napieralski products in good yields which then isomerise readily to afford N-acylaminol ethers under base catalysis; acyliminium ions are then generated using trimethylsilyl triflate and captured, for example with allyltrimethylsilane.

引用

页码：2751 / 2752

页数：2

共 11 条

[1]

BROWN DS, 1990, SYNLETT, P619

[2]

CHEUNG GK, 1991, SYNLETT, P721

[3]

CHEUNG GK, 1992, SYNLETT, P77

[4]

COOPER MS, 1990, SYNLETT, P617

[5] A new synthesis of oxyberberine and a synthesis of palmatine [J].

Haworth, RD ;

Koepell, JB ;

Perkin, WH .

JOURNAL OF THE CHEMICAL SOCIETY, 1927, :548-554

[6]

HAWORTH RD, 1925, J CHEM SOC, P1709

[7]

Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047

[8]

KAMETANI T, 1981, CHEM HETEROCYCL COMP, P139

[9] Synthesis of oxydehydrocorydaline [J].

Koepfli, JB ;

Perkin, WH .

JOURNAL OF THE CHEMICAL SOCIETY, 1928, :2989-3000

[10]

Shamma M, 2012, ISOQUINOLINE ALKALOI, V25

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