“Four-component” assembly of polyaromatic 4H-cyclopenta[b]thiophene structures based on GaCl3-promoted reaction of styrylmalonates with 5-phenylthiophene-2-carbaldehyde

“Four-component” assembly of polyaromatic 4H-cyclopenta[b]thiophene structures based on GaCl3-promoted reaction of styrylmalonates with 5-phenylthiophene-2-carbaldehyde Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2019, Volume: 60, Number: 10, Pages: 746-750 Pages count : 5 DOI: 10.1016/j.tetlet.2019.02.007

Authors

Borisov Denis D. ¹ , Chermashentsev Grigory R. ¹ , Novikov Roman A. ¹ , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

New “four-component” self-assembly of polyaromatic thiophene structures based on styrylmalonates and 5-phenylthiophene-2-carbaldehyde has been developed. This process is promoted by GaCl3 and involves two [2 + 3]-annulation steps on the CHO-groups and para-substitution into one Ph-ring. The main feature of discovered process is a high diastereoselectivity with a significant increase in molecular complexity. The resulting polyaromatic structures containing two thiophene moieties in each structure have intense color and strong absorption in a near UV spectral region with absorption maxima in the range of 257–360 nm.

Borisov D.D. , Chermashentsev G.R. , Novikov R.A. , Tomilov Y.V.
“Four-component” assembly of polyaromatic 4H-cyclopenta[b]thiophene structures based on GaCl3-promoted reaction of styrylmalonates with 5-phenylthiophene-2-carbaldehyde
Tetrahedron Letters. 2019. V.60. N10. P.746-750. DOI: 10.1016/j.tetlet.2019.02.007 WOS Scopus OpenAlex

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