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

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 19, 2024

Abstract Herein we report for the first time a sunlight‐driven, irreversible photocyclization reaction of indole‐linked trisubstituted thiazoles, synthesis highly fluorescent thiazole‐fused benzo[ ]carbazoles using mixture solvents (CH 3 CN: DMSO; : 1). Ring opening indole moiety was observed in case thiazole derivatives having 2‐methyl substituents. Under similar conditions, thiazoles cyclic 1,3‐dicarbonyls place also worked. This provides products two medicinally important moieties and benzocarbazoles. We have studied photophysical properties all found that most synthesized very good fluorescence quantum yields.

Язык: Английский

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Iodine‐Catalyzed Cascade Reaction of 2‐Styrylbenzaldehydes with Indoles in the Synthesis of 1H‐Indenes via 4π‐Electrocyclization

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1436 - 1441

Опубликована: Янв. 23, 2024

Abstract A cascade reaction between 2‐styrylbenzaldehydes and indoles has been developed for the synthesis of 1 H ‐indenes. An iodine‐catalyzed nucleophilic addition to an aldehyde group leads formation carbocation intermediates that undergo 4π‐electrocyclization give indenes with a trisubstituted double bond. These are transformed into thermodynamically more stable products fully substituted bond under conditions. Minor quantities indolylbenzo[ b ]carbazoles also produced as by‐products.

Язык: Английский

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Iodine-Catalyzed Regioselective Synthesis of Diphenyl-Substituted Carbazoles via [4 + 2] Annulation of β-Formyl Ketones with Indoles

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17505 - 17510

Опубликована: Ноя. 30, 2023

The [4 + 2] annulation of β-formyl ketones with an indole has been developed for the regioselective synthesis diphenyl-substituted carbazoles in presence a catalytic amount iodine. 1,4-dicarbonyl compound containing phenyl group at α-position aldehyde reacts more readily indoles to form carbazole derivatives. Using this method, variety derivatives can be accessed under mild reaction conditions.

Язык: Английский

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Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Chemistry - A European Journal, Год журнала: 2023, Номер 30(8)

Опубликована: Ноя. 30, 2023

Carbazole is a heterocyclic motif that can be found in diverse array of natural and unnatural products displaying wide range biological physiological properties. Furthermore, this heterocycle part electronic materials like photoconducting polymers organic optoelectronic owing to its excellent photophysical characteristics. Consequently, the development synthetic strategies for carbazole scaffolds holds potential significance material fields. In regard, variety preparation methods has been developed exploit their efficient distinct formation new C-C C-heteroatom bonds under mild conditions enabling broad substrate diversity functional group tolerance. Therefore, review focuses on synthesis set derivatives describing methodologies involve direct irradiation, photosensitization, photoredox, electrochemical thermal cyclization reactions.

Язык: Английский

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Dibenzo‐Fused Heterocycles: A Decade Update on the Syntheses of Carbazole, Dibenzofuran, and Dibenzothiophene

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Сен. 6, 2024

Abstract Polycyclic heterocycles are the most common and critical structural motifs found in a variety of natural products, medicines, fertilizers, advanced materials. Because their widespread use biologically active compounds material chemistry, functionalised dibenzo heterocyclic compounds, especially dibenzofuran, dibenzothiophene, carbazole derivatives, garnered much attention over time. Scientists interested elucidating more efficient techniques for developing these industrially essential compounds. Dibenzo‐fused can rapidly be synthesised using highly transition metal‐catalysed strategies as well by economic metal‐free reaction conditions. This review includes detailed overview recent significant synthetic techniques, both metal‐free, to produce medicinally important dibenzo‐fused heterocycles.

Язык: Английский

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Indole Substrates to Carbazole Targets: An Update in the Discovery of an Ideal Synthetic Methodology

Journal of Molecular and Engineering Materials, Год журнала: 2023, Номер 11(03n04)

Опубликована: Ноя. 15, 2023

Carbazole compounds have been proven to exhibit vital photophysical and biological applications. Even simple carbazole derivatives were showing attractive activities such as antimicrobacterial activity (Glycozoline), antiproliferative (Mukonine), free radical scavenger (Carazostatin), etc. In case of applications, utilized in organic semiconductors, photoconducting polymers, Green host material phosphorescent light-emitting diodes (OLEDs), hole-transporting OLEDs light emitting materials. An account different synthetic methodologies involved the synthesis natural was evaluated based on usage commercially available cheap starting materials Indole. This paper takes into time from 2011 2023. The advanced methods developed 12 principles chemistry Multistep domino reactions, Atom & Step economy protection-free mild reaction conditions, open atmosphere harmless by-products photochemical transformations.

Язык: Английский

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One-pot and metal-free synthesis of atropisomeric carbazolyl-indoles by a facile [4 + 2]-benzannulation in ethanol and investigation of their photoluminescence property

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3397 - 3403

Опубликована: Янв. 1, 2024

In this article, a series of atropisomeric carbazolyl-indoles were synthesized through one-pot, green method, and their photoluminescence properties investigated.

Язык: Английский

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Au(i)/Sc(iii)-co-catalyzed tandem spiroannulation/cycloisomerization of 3-(2-ethynylaryl)-N-tosylaziridines with indoles to access 5H-benzo[b]carbazoles

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(29), С. 5999 - 6003

Опубликована: Янв. 1, 2024

An unusual Au( i )/Sc( iii )-co-catalyzed tandem spiroannulation/cycloisomerization of 3-(2-ethynylaryl)- N -tosylaziridine-2,2-diesters with indoles has been reported. A variety 5 H -benzo[ b ]carbazoles were obtained in moderate to good yields (30–88%).

Язык: Английский

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