Efficient synthesis of highly oxygenated benzo[g]chrysenes

被引：14

作者：

Chang, Meng-Yang ^{[1
]}

Chen, Yi-Chia ^{[1
]}

Chan, Chieh-Kai ^{[1
]}

Huang, Genin Gary ^{[1
]}

机构：

[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan

来源：

TETRAHEDRON | 2015年 / 71卷 / 14期

关键词：

Benzannulation; Benzo[g]chrysenes; Naphthalenes; ORGANIC-SYNTHESIS; DIOL; CYCLODEHYDROGENATION; HYDROCARBONS; DERIVATIVES; BOND;

D O I：

10.1016/j.tet.2015.02.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sc(OTf)(3)-mediated one-pot benzannulation of oxygenated phenylacetic acids 3 with oxygenated benzenes 2 in the presence of Tf2O in MeCN at rt for 3 h afforded a series of polyoxygenated benzo[g] chrysenes 1 and naphthalenes 5 with moderate to good yields under the photolytic irradiation condition. The facile transformation proceeds by a cascade sequence starting with a double Friedel Crafts acylation of skeleton 2 with 3, followed by a double Scholl ring-closure and then, an O-acylation. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2095 / 2104

页数：10

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