Research output: Contribution to journal › Article › peer-review
Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings. / Mosiagin, Ivan P.; Tomashenko, Olesya A.; Spiridonova, Darya V.; Novikov, Mikhail S.; Tunik, Sergey P.; Khlebnikov, Alexander F.
In: Beilstein Journal of Organic Chemistry, Vol. 17, 23.06.2021, p. 1490-1498.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings
AU - Mosiagin, Ivan P.
AU - Tomashenko, Olesya A.
AU - Spiridonova, Darya V.
AU - Novikov, Mikhail S.
AU - Tunik, Sergey P.
AU - Khlebnikov, Alexander F.
N1 - Publisher Copyright: © 2021 Mosiagin et al.; licensee Beilstein-Institut. License and terms: see end of document. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.
PY - 2021/6/23
Y1 - 2021/6/23
N2 - 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-bromo-phenyl)-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.
AB - 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-bromo-phenyl)-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.
KW - Arylation
KW - Pyridine
KW - Pyrrole
KW - Radical cyclization
KW - Tris(trimethylsilyl)silane
KW - tris(trimethylsilyl)silane
KW - radical cyclization
KW - pyridine
KW - arylation
KW - pyrrole
UR - http://www.scopus.com/inward/record.url?scp=85108889056&partnerID=8YFLogxK
U2 - 10.3762/bjoc.17.105
DO - 10.3762/bjoc.17.105
M3 - Article
AN - SCOPUS:85108889056
VL - 17
SP - 1490
EP - 1498
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -
ID: 78677826