Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

Standard

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.

в: Beilstein Journal of Organic Chemistry, Том 17, 23.06.2021, стр. 1490-1498.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{89ddb9cee1954b9086c6b9161b368f47,

title = "Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings",

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-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.",

keywords = "Arylation, Pyridine, Pyrrole, Radical cyclization, Tris(trimethylsilyl)silane, tris(trimethylsilyl)silane, radical cyclization, pyridine, arylation, pyrrole",

author = "Mosiagin, {Ivan P.} and Tomashenko, {Olesya A.} and Spiridonova, {Darya V.} and Novikov, {Mikhail S.} and Tunik, {Sergey P.} and Khlebnikov, {Alexander F.}",

year = "2021",

month = jun,

day = "23",

doi = "10.3762/bjoc.17.105",

language = "English",

volume = "17",

pages = "1490--1498",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

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.

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