Synthesis of Highly Fluorescent Thiazole Fused Benzo[<i>a</i>] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles

Abstract 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 (CH 3 CN: 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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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-11-19
DOI
https://doi.org/10.1002/ejoc.202400972
Citations
4
Primary Topic
Photochromic and Fluorescence Chemistry
Type
article
Field-Weighted Citation Impact
0.47

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article

Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles

Prabhas Bhaumick, Lokman Hakim Choudhury, Nurabul Mondal
4 citations
European Journal of Organic Chemistry
Photochromic and Fluorescence Chemistry
0.47
article

Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles

Prabhas Bhaumick, Lokman Hakim Choudhury, Nurabul Mondal
article en
4 citations

Abstract

Abstract 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 (CH 3 CN: 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.

European Journal of Organic ChemistryVol. 27(48)
Indian Institute of Technology Patna (IN)
Arthritis National Research Foundation, Indian Institute of Technology, Patna, Department of Science and Technology, Ministry of Science and Technology, India
Openalex Percentile: Top 37%
Photochromic and Fluorescence Chemistry
0.47
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Synthesis of Highly Fluorescent Thiazole Fused Benzo[<i>a</i>] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles — Prabhas Bhaumick, Lokman Hakim Choudhury, et al. · European Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS