通过吲哚噻唑的日光驱动光环化合成高荧光噻唑融合苯并[a]咔唑

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-20 DOI:10.1002/ejoc.202400972
Prabhas Bhaumick, Nurabul Mondal, Lokman H. Choudhury
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摘要

在此,我们首次报道了吲哚连接的三取代噻唑在阳光驱动下的不可逆光环化反应,该反应使用混合溶剂(CH3CN: DMSO; 3 : 1)合成了高荧光噻唑融合苯并[a]咔唑。在具有 2-甲基吲哚取代基的噻唑衍生物中观察到了吲哚分子的开环。在类似的反应条件下,以环状 1,3-二羰基取代吲哚基的三取代噻唑的光环化反应也起作用。该反应提供了具有噻唑和苯并咔唑两种重要药用分子的产物。我们研究了所有产物的光物理特性,发现大多数合成产物都具有非常好的荧光量子产率。
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Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles
Herein we report for the first time a sunlight‐driven, irreversible photocyclization reaction of indole‐linked trisubstituted thiazoles, for the synthesis of highly fluorescent thiazole‐fused benzo[a]carbazoles using a mixture of solvents (CH3CN: DMSO; 3 : 1). Ring opening of indole moiety was observed in the case of thiazole derivatives having 2‐methyl indole substituents. Under similar reaction conditions, photocyclization of trisubstituted thiazoles having cyclic 1,3‐dicarbonyls in place of indole moiety also worked. This reaction provides products having two medicinally important moieties thiazole and benzocarbazoles. We have studied the photophysical properties of all the products and found that most of the synthesized products have very good fluorescence quantum yields.
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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