Open Access
Beilstein Journal of Organic Chemistry, volume 17, pages 1490-1498
Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings
Publication type: Journal Article
Publication date: 2021-06-23
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.7
ISSN: 18605397
PubMed ID:
34239616
Organic Chemistry
Abstract
A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o-bromophenyl-substituted pyrrolylpyridinium salts using the (TMS)3SiH/AIBN system. The cyclization provides generally good yields of pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline hydrobromides having no additional radical-sensitive substituents. The free bases can be obtained from the synthesized hydrobromides in quantitative yield by basification at room temperature. The selectivity control of intramolecular arylation was achieved by replacing the halogen: the use of 1-(2-(ortho-bromophenyl)-4-(ortho-iodophenyl)pyrrol-3-yl)pyridinium bromide makes it possible to obtain a monocyclization product, and the bicyclization product from the dibromo derivative. The procedure is also applicable to obtain 3-arylpyrido[2,1-a]pyrrolo[3,2-c]isoquinoline derivatives including 2-unsubstituted skeletons that are inaccessible via Pd-catalyzed cyclization.
Citations by journals
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1
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Chemistry - An Asian Journal
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Chemistry - An Asian Journal
1 publication, 50%
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European Journal of Organic Chemistry
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European Journal of Organic Chemistry
1 publication, 50%
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1
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Citations by publishers
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1
2
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Wiley
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Wiley
2 publications, 100%
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1
2
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Mosiagin I. P. et al. Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings // Beilstein Journal of Organic Chemistry. 2021. Vol. 17. pp. 1490-1498.
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Mosiagin I. P., Tomashenko O. A., Spiridonova D. V., Novikov M. S., Tunik S. P., Khlebnikov A. F., Novikov M. S. Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings // Beilstein Journal of Organic Chemistry. 2021. Vol. 17. pp. 1490-1498.
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TY - JOUR
DO - 10.3762/bjoc.17.105
UR - https://doi.org/10.3762%2Fbjoc.17.105
TI - Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings
T2 - Beilstein Journal of Organic Chemistry
AU - Mosiagin, I P
AU - Tomashenko, Olesya A
AU - Spiridonova, Darya V.
AU - Novikov, Mikhail S.
AU - Tunik, Sergey P.
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2021
DA - 2021/06/23 00:00:00
PB - Beilstein-Institut
SP - 1490-1498
VL - 17
PMID - 34239616
SN - 1860-5397
ER -
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@article{2021_Mosiagin,
author = {I P Mosiagin and Olesya A Tomashenko and Darya V. Spiridonova and Mikhail S. Novikov and Sergey P. Tunik and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings},
journal = {Beilstein Journal of Organic Chemistry},
year = {2021},
volume = {17},
publisher = {Beilstein-Institut},
month = {jun},
url = {https://doi.org/10.3762%2Fbjoc.17.105},
pages = {1490--1498},
doi = {10.3762/bjoc.17.105}
}