Abstract: 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.

Cite: Ulyankin E.B. , Bogza Y.P. , Kostyuchenko A.S. , Chernenko S.A. , Yurpalov V.L. , Shatsauskas A.L. , Samsonenko A.L. , Fisyuk A.S.
Photochemical synthesis of 4H-thieno[3,2-c]chromene and their optical properties
Synlett. 2021. V.32. P.790-794. DOI: 10.1055/a-1392-2209 WOS Scopus РИНЦ OpenAlex

Dates:

Submitted:	Jan 16, 2021
Accepted:	Feb 16, 2021
Published online:	Feb 16, 2021
Published print:	May 1, 2021

Identifiers:

Web of science:	WOS:000626718500001
Scopus:	2-s2.0-85102487937
Elibrary:	46578557
OpenAlex:	W3132742041

Citing:

DB	Citing
Scopus	2
Web of science	1
OpenAlex	4

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