Copper-Catalyzed Annulation of Electrophilic Benzannulated Heterocycles with 2-Aminopyridine and 2-Aminoquinoline: Direct Access toward Polyring-Fused Imidazo[1,2-a]pyridines

被引：9
|
作者：
Babu, Sheba Ann [1 ,2 ]
Varsha, P. V. [1 ]
Poulose, Susanna [1 ,2 ]
Varughese, Sunil [1 ,2 ]
John, Jubi [1 ,2 ]
机构：
[1] CSIR Natl Inst Interdisciplinary Sci & Technol CSI, Chem Sci & Technol Div, Thiruvananthapuram 695019, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 14期
关键词：
FIELD-EFFECT TRANSISTORS; METAL-FREE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; HIGH-PERFORMANCE; 3-NITROINDOLES; DERIVATIVES; PALLADIUM; AMINOPYRIDINES; NITROOLEFINS; HETEROACENES;
D O I：
10.1021/acs.joc.3c00849
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a direct method for the synthesis ofpolyring-fusedimidazo[1,2-a]pyridines via a copper-catalyzed annulationof electrophilic benzannulated heterocycles with 2-aminopyridine and2-aminoquinoline. From 3-nitroindoles and 2-aminopyridine, we couldsynthesize tetracenes, viz., indole-fused imidazo[1,2-a]pyridines, and by starting from 2-aminoquinoline, we could generatepentacenes, viz., indolo-imidazo[1,2-a]quinolines.In addition, we could also extend the methodology toward the synthesisof benzothieno-imidazo[1,2-a]pyridines starting from3-nitrobenzothiophene. Furthermore, the basic photophysical propertiesof these synthesized heteroacenes were evaluated.
引用
收藏
页码：10027 / 10039
页数：13
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