Synthesis and optical properties of 2-functionally substituted 4,5-dihydrothieno[3,2-c]quinolines

Bogza, Y. P.; Rastrepin, Alexey A.; Нидер, В. В.; Zheleznova, Tatyana Yu.; Stasyuk, Anton J.; Kurowska, Aleksandra; Łaba, Katarzyna; Ulyankin, Evgeny B.; Domagała, Wojciech; Fisyuk, A. S.

doi:10.1016/j.dyepig.2018.06.031

Cited by 9 publications

(2 citation statements)

References 48 publications

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“…Only in the case of 6e were the isomeric 4H-thieno [3,2-c]chromene-2-carbaldehydes 7e (entry 6) and 7p (entry 17) obtained in a 2:5 ratio according to NMR data. However, compound 7e was the main product in the case of Pd-catalyzed cyclization 6e using method D. 12 The UV spectra of 4H-thieno [3,2-c]chromene-2-carbaldehydes have been reported only for compounds 7a-f. 19 The main emission band in the luminescence spectra of Figure 3 In situ experimental (black curves) and simulated (red curves) EPR spectra of glass solutions of compounds 6a (Spectrum 1) and 5a (Spectrum 2) in acetonitrile after UV irradiation at 77 K…”

Section: Letter Synlettmentioning

confidence: 99%

Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties

Ulyankin

Bogza

Kostyuchenko

et al. 2021

Synlett

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4 - [(2-Iodalyloxy) methyl] thiophene-2-carbaldehyde and 5-iodo-4- (aryloxymethyl)thiophene-2-carbaldehydes were obtained by interaction of phenols with 4-chloromethylthiophene-2-carbaldehyde and its 5-iodosubstituted derivative. These compounds underwent ring closure upon irradiation with UV light (254 nm) to form 4H-thieno[3,2-c]chromene-2-carbaldehyde in high yield. The formation of intermediate radical species was detected by EPR method. Comparative analysis of the ring closure methods showed that the photochemical cyclization of 5-iodo-4-(aryloxymethyl) thiophene-2-carbaldehyde is more rational than the Pd-catalyzed intramolecular arylation. A series of substituted 4H-thieno[3,2-c]chromene-2-carbaldehydes was synthesized by the photochemical cyclization of the corresponding precursors. The photophysical properties of the synthesized compounds were studied. The obtained 4H-thieno[3,2-c]chromene-2-carbaldehydes can be used as covert marking pigments.

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Section: Letter Synlettmentioning

confidence: 99%

Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties

Ulyankin

Bogza

Kostyuchenko

et al. 2021

Synlett

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“…Biological activities, such as anticancer [ 1 , 2 ], antimicrobial [ 3 , 4 , 5 ], anti-Alzheimer’s [ 6 ], antioxidant [ 7 ], and cardiovascular [ 8 ], can be highlighted. These nuclei can be found in natural compounds [ 9 , 10 , 11 , 12 ] and synthetic materials [ 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds

et al. 2020

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Chromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excellent yields through the Vilsmeyer-Haack reaction of flavanones and azaflavanones. Protocols towards the synthesis of new heterocycles, such as 3H-chromeno[3–c]quinolines, (Z/E)-2-aryl-4-chloro-3-styryl-2H-chromenes, and (E)-2-aryl-4-chloro-3-styrylquinoline-1(2H)-carbaldehydes were established. Altogether, we demonstrate the value of chromene- and quinoline-3-carbaldehydes as building blocks.

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Synthesis of Polycyclic Quinolines by Means of Brønsted Acid Mediated Reaction of β‐(2‐Aminophenyl)‐α,β‐Ynones with Ketones

et al. 2019

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Synthesis and optical properties of 2-functionally substituted 4,5-dihydrothieno[3,2-c]quinolines

Cited by 9 publications

References 48 publications

Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties

Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties

Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds

Synthesis of Polycyclic Quinolines by Means of Brønsted Acid Mediated Reaction of β‐(2‐Aminophenyl)‐α,β‐Ynones with Ketones

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