Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

被引：76

作者：

Baum, SM

Trabanco, AA

Montalban, AG

Micallef, AS

Zhong, C

Meunier, HG

Suhling, K

Phillips, D

White, AJP

Williams, DJ

Barrett, AGM ^{[1
]}

Hoffman, BM

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

[2] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

[3] Assumption Coll, Dept Chem, Worcester, MA 01609 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 05期

关键词：

D O I：

10.1021/jo026484u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The novel five- and seven-membered ring appended aminoporphyrazines 3 and 12 have been prepared via mixed Linstead macrocyclization. The structures of both have been unequivocally established by X-ray crystallographic studies. Reductive deselenation of selenadiazole 3 in the presence of 9,10-phenanthrenequinone or 2,3-butanedione results in the formation of pyrazines 6a,b, whereas oxidation of porphyrazine 12 gave the corresponding seco derivative 14. seco-Porphyrazine 14 mediates the generation of singlet oxygen with a quantum yield of 0.74.

引用

页码：1665 / 1670

页数：6

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