Synthesis of naphtho[2,3-b]indolizine-6,11-dione derivatives by iodine oxidation of 2-alkyl-1,4-naphthoquinones in the presence of substituted pyridines

被引：16

作者：

Citterio, A

Fochi, M

Marion, A

Mele, A

Sebastiano, R

Delcanale, M

机构：

[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy

[2] Chiesi Farmaceut SPA, I-43100 Parma, Italy

来源：

HETEROCYCLES | 1998年 / 48卷 / 10期

关键词：

D O I：

10.3987/COM-98-8228

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodine oxidation of 2-alkyl-1,4-naphthoquinones (1) in the presence of substituted pyridines (2) afforded naphtho[2,3-b]indolizine-6,11-dione derivatives (3). Other oxidant systems (MnO2/I- or Fe(ClO4)(3))/I-2) can be used and 2-alkylbenzoquinones reacted in lower yield. Iodination of 3 by I, and dibenzoyl peroxide occurred selectively at position 12.

引用

页码：1993 / 2002

页数：10

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[2]

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[3]

AYYANGAR NR, 1979, STUD ORG CHEM AMSTER, V3, P34

[4] STRUCTURES OF CHARGE-PERTURBED OR STERICALLY OVERCROWDED MOLECULES .17. THE SINGLE-CRYSTAL STRUCTURE OF AN ORGANIC TETRACATION - TETRAKIS(4-DIMETHYLAMINOPYRIDINIUM)-PARA-BENZOQUINONE TETRAKIS(TRIFLATE) [J].