Synthesis of polybenzoquinazolines via an intramolecular dehydration of photocyclization
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- 作者：Wei Weia ; b ; c ; Chenchen Lia ; b ; c ; Tao Wanga ; b ; c ; Dian Liua ; b ; c ; Zunting Zhanga ; b ; c ; zhangzunting@sina.com" class="auth_mail" title="E-mail the corresponding author
- 关键词：Photocyclization ; Intramolecular dehydration ; Benzo[h]-naphth[1 ; 2-f]quinazolines ; Benzo[h]-phenanthren[9 ; 10-f]quinazoines
- 刊名：Tetrahedron
- 出版年：2016
- 出版时间：18 August 2016
- 年：2016
- 卷：72
- 期：33
- 页码：5037-5046
- 全文大小：770 K
文摘
Benzo[h]-naphth[1,2-f]quinazolines and benzo[h]-phenanthren[9,10-f]quinazoines were synthesized from intermediates 4-(2-hydroxyphenyl)-5-(naphthalen-1-yl)pyrimidines and 4-(2-hydroxyphenyl)-5-(phenanthren-1-yl) pyrimidines by the intramolecular dehydration of photocyclization. The intermediates were obtained by the condensation of 3-arylchromone with formamidine, acetamidine or guanidine refluxing in ethanol, respectively. Irradiation of the corresponding intermediates by a high-pressure mercury lamp in 19:1 (v/v) EtOH
H2O or 18:1:1 (v/v) EtOHH2O-Dioxane lead to target products. This photocyclization showed advantages including catalyst-free and mild reaction condition. Moreover, water was the only by-product of this reaction. The crystal structure of 2-amino-12-methoxy-benzo[h]-naphth[1,2-f]quinazoline was determined and the fluorescence properties of these polybenzoquinazolines were also investigated.
H2O or 18:1:1 (v/v) EtOHH2O-Dioxane lead to target products. This photocyclization showed advantages including catalyst-free and mild reaction condition. Moreover, water was the only by-product of this reaction. The crystal structure of 2-amino-12-methoxy-benzo[h]-naphth[1,2-f]quinazoline was determined and the fluorescence properties of these polybenzoquinazolines were also investigated.