Effective Synthesis of Hard-To-Reach 3,4-Disubstituted Thiophene Derivatives Based on bis(2-chloropropenyl) Sulfide

An efficient approach for the synthesis of hard-to-reach 3,4-disubstituted thiophene derivatives: 4,5,9,10-tetrahydrothieno[3',4;5,6]-cycloocta[1,2- c ]thiophene, 1 H ,4 H -thieno[3,4- d ][1,2]dioxine, 4-(hydroxymethyl)thiophene-3-carbaldehyde, based on consecutive transformations of bis(2-chlo...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-10, Vol.56 (10), p.1292-1296
Main Authors: Nikonova, Valentina S., Korchevin, Nikolai А., Borodina, Tat’yana N., Smirnov, Vladimir I., Albanov, Aleksander I., Rozentsveig, Igor B.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary:An efficient approach for the synthesis of hard-to-reach 3,4-disubstituted thiophene derivatives: 4,5,9,10-tetrahydrothieno[3',4;5,6]-cycloocta[1,2- c ]thiophene, 1 H ,4 H -thieno[3,4- d ][1,2]dioxine, 4-(hydroxymethyl)thiophene-3-carbaldehyde, based on consecutive transformations of bis(2-chloropropenyl) sulfide has been found. Transformations were realized without isolation of the intermediate compounds. The reactivity of 4,5,9,10-tetrahydrothieno[3',4;5,6]cycloocta[1,2- c ]thiophene has been studied based on the example of acetylation reaction, and the possibility of obtaining bifunctional derivatives with the participation of both thiophene rings has been shown. The structure of some synthesized compounds has been studied with X-ray diffraction method.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02813-2