Photocyclization synthesis of phenanthridine and its derivatives under direct dehydrogenation conditions

被引：6

作者：

Zhu, Wen-Qing ^{[1
]}

Zhang, Jin ^{[1
]}

Fan, Pan ^{[1
]}

Shi, Lan-Ting ^{[1
]}

Li, Hong ^{[1
]}

Yang, Min-Ge ^{[1
]}

Li, Yang ^{[1
]}

机构：

[1] Xian Polytech Univ, Sch Enviromental & Chem Engn, Xian Key Lab Text Chem Engn Auxiliaries, 19 Jinhua South Rd, Xian 710048, Shaanxi, Peoples R China

来源：

TETRAHEDRON LETTERS | 2021年 / 64卷

基金：

中国国家自然科学基金;

关键词：

Phenanthridine; Photocyclization reaction; Diphenylformimine; Tert-butanol; ONE-POT SYNTHESIS; CATALYZED 3-COMPONENT REACTION; 6-SUBSTITUTED PHENANTHRIDINES; OXIDATIVE CYCLIZATION; ARYLBORONIC ACIDS; ISOCYANIDE INSERTION; AROMATIC-ALDEHYDES; ALKYNES SYNTHESIS; DIRECT ACCESS; METAL-FREE;

D O I：

10.1016/j.tetlet.2020.152734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for synthesizing phenanthridines by photocyclization has been established. This method does not require inert gas protection, does not require transition metal catalysts and is environmentally friendly, efficient and convenient. It is proposed to use (E)-N,1-diphenylformimines as substrates to synthesize phenanthridine and its derivatives by ultraviolet light, which provides a new synthesis route for further research on the synthesis of phenanthridines by photocyclization. Eight new phenanthridine compounds were synthesized. The confirmation of their structures provides a material basis for further study of their properties and tapping of their potential for applications. The establishment of this method further broadens the synthetic pathways of phenanthridine compounds. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：4

共 50 条

[1] ENAMIDE PHOTOCYCLIZATION IN SYNTHESIS OF BENZO[C]PHENANTHRIDINE ALKALOIDS
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YAMAMOTO, O
KIGUCHI, T
NAITO, T
ISHII, H
HETEROCYCLES, 1977, 6 (9-10) : 1730 - 1734
[2] A NEW SYNTHESIS OF PHENANTHRIDINE DERIVATIVES
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[4] THE CHEMISTRY OF PHENANTHRIDINE AND ITS DERIVATIVES
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