Palladium-catalyzed cascade reactions in aqueous media: synthesis and photophysical properties of pyrazino-fused quinazolinones. Issue 2 (7th December 2020)

• Record Type: Journal Article
• Authors: Zhang, Yetong; Xiong, Wenzhang; Chen, Lepeng; Shao, Yinlin; Li, Renhao; Chen, Zhongyan; Ge, Jingyuan; Lv, Ningning; Chen, Jiuxi
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 2(2021)
• Page Start: 304
• Page End: 309
• Publication Date: 2020-12-07
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo01244k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A convenient, efficient, and direct approach toward the synthesis of pyrazino-fused quinazolinone frames has been developed. The photophysical properties of 3e with the AIE effect were investigated. Abstract : Heterocycle-fused quinazolinone derivatives have attracted great attention due to their diversified biological and optical activities. In this study, a novel one-pot palladium-catalyzed cascade C–C coupling/cyclization/aromatization of 2-(4-oxoquinazolin-3(4 H )-yl)acetonitrile derivatives with arylboronic acids has been disclosed to synthesize 1, 3-diaryl-6 H -pyrazino[2, 1- b ]quinazolin-6-one in water. This protocol provides an efficient access to valuable pyrazino-fused quinazolinones in a green solvent ( i.e., water) with yields ranging from moderate to excellent. Furthermore, the photophysical properties of these molecules were investigated. The resultant pyrazino-fused quinazolinones exhibit tunable fluorescence, and 3e displays the aggregation induced emission properties with a large Stokes shift. This study provides a useful approach to the development of pyrazino-fused quinazolinones, which have potential applications in chemistry, biology, and materials science.