volume 53 issue 14 pages 2422-2434

A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives

Evgeny B. Ulyankin 1, 2
Anastasia S. Kostyuchenko 1, 2
Sergey A. Chernenko 1, 2
Mikhail O. Bystrushkin 1, 2
Anna L. Samsonenko 1, 2
Publication typeJournal Article
Publication date2021-03-08
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 1437210X
Catalysis
Organic Chemistry
Abstract

A new approach to the synthesis of fused benzothiophene derivatives was developed based on iodine-promoted photocyclization of 4,5-diaryl-substituted thiophenes obtained in three steps from commercially­ available compounds. Comparative analysis showed that photochemical cyclization is a more efficient method for the preparation of fused benzo[b]thiophene derivatives, compared to oxidative coupling of 4,5-diaryl-substituted thiophenes in the presence of iron(III) chloride and palladium-catalyzed intramolecular arylation. This new approach provides an efficient synthesis of functionally substituted naphtho[2,1-b:3,4-b′]dithiophenes, phenanthro[9,10-b]thiophenes, benzo[1,2-b:3,4-b′:6,5-b′′]trithiophenes, as well as new fused heterocycles containing a pyridine ring and/or a carbazole moiety.

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GOST |
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GOST Copy
Fisyuk A. S. et al. A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives // Synthesis. 2021. Vol. 53. No. 14. pp. 2422-2434.
GOST all authors (up to 50) Copy
Fisyuk A. S., Ulyankin E. B., Kostyuchenko A. S., Chernenko S. A., Bystrushkin M. O., Samsonenko A. L., Shatsauskas A. L. A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives // Synthesis. 2021. Vol. 53. No. 14. pp. 2422-2434.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/a-1416-4924
UR - https://doi.org/10.1055/a-1416-4924
TI - A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives
T2 - Synthesis
AU - Fisyuk, Alexander S.
AU - Ulyankin, Evgeny B.
AU - Kostyuchenko, Anastasia S.
AU - Chernenko, Sergey A.
AU - Bystrushkin, Mikhail O.
AU - Samsonenko, Anna L.
AU - Shatsauskas, Anton L.
PY - 2021
DA - 2021/03/08
PB - Georg Thieme Verlag KG
SP - 2422-2434
IS - 14
VL - 53
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Fisyuk,
author = {Alexander S. Fisyuk and Evgeny B. Ulyankin and Anastasia S. Kostyuchenko and Sergey A. Chernenko and Mikhail O. Bystrushkin and Anna L. Samsonenko and Anton L. Shatsauskas},
title = {A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives},
journal = {Synthesis},
year = {2021},
volume = {53},
publisher = {Georg Thieme Verlag KG},
month = {mar},
url = {https://doi.org/10.1055/a-1416-4924},
number = {14},
pages = {2422--2434},
doi = {10.1055/a-1416-4924}
}
MLA
Cite this
MLA Copy
Fisyuk, Alexander S., et al. “A Simple and Efficient Synthesis of Fused Benzo[b]thiophene Derivatives.” Synthesis, vol. 53, no. 14, Mar. 2021, pp. 2422-2434. https://doi.org/10.1055/a-1416-4924.