Synthesis of Luminescent Indolo[2,1-b]quinazolin-6(12H)-ones via a Sequential Ugi/Iodine-Promoted Cyclization/Staudinger/Aza-Wittig Reaction

被引：7
|
作者：
Yang, Mao-Lin [1 ]
Zhao, Long [1 ]
Chen, Hao-Ran [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Natl Key Lab Green Pesticide, Hubei Int Sci & Technol Cooperat Base Pesticide &, Wuhan 430079, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 23期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; TRYPTANTHRINS; CYCLIZATION; PHARMACOPHORE; CASCADE; ISATINS; DYES; UGI;
D O I：
10.1021/acs.joc.3c01955
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new efficient synthesis of indolo-[2,1-b]-quinazolin-6-(12H)-ones via a sequential Ugi/iodine-promoted cyclization/Staudinger/aza-Wittig reaction was developed. The acid catalyzed three-component reactions of 2-azidobenzaldehydes, 2-[2-(trimethylsilyl)-ethynyl]-benzenamines (or o-aminoacetophenones), and isocyanides gave Ugi-3CR intermediates, which reacted subsequently with I-2/DMSO and triphenylphosphine to produce indolo-[2,1-b]-quinazolin-6-(12H)-ones in good overall yields. The obtained indolo-[2,1-b]-quinazolin-6-(12H)-ones were all colored in bright red or orange. Their luminescent property was studied preliminarily and some of them showed high molar absorption coefficients, strong fluorescence emission intensity, and good absolute light quantum yields.
引用
收藏
页码：16424 / 16434
页数：11
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