Tunable Zinc-Mediated Reductive Cyclization of Diastereomeric 3-Nitro-4-phenacyl-2-(trihalomethyl)chromanes to Fused Pyrroline N-Oxides, Pyrrolines, and Pyrrolidines

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Tunable Zinc-Mediated Reductive Cyclization of Diastereomeric 3-Nitro-4-phenacyl-2-(trihalomethyl)chromanes to Fused Pyrroline N-Oxides, Pyrrolines, and Pyrrolidines. / Korotaev, Vladislav ; Kutyashev, Igor; Sannikov, Maxim и др.
в: Journal of Organic Chemistry, Том 89, № 3, 2024, стр. 1567-1590.

Результаты исследований: Вклад в журнал › Статья › Рецензирование

BibTeX

@article{d2e20b7f03094d5cb09fd237aeeac18a,

title = "Tunable Zinc-Mediated Reductive Cyclization of Diastereomeric 3-Nitro-4-phenacyl-2-(trihalomethyl)chromanes to Fused Pyrroline N-Oxides, Pyrrolines, and Pyrrolidines",

abstract = "Reductive cyclization of trans,trans- and trans,cis-isomers of the 2-CF3-substituted 3-nitro-4-phenacylchromanes with Zn-based reductive systems, depending on the conditions, affords 4-CF3-substituted 1,3a,4,9b-tetrahydrochromeno-[3,4-b]-pyrrole 3-oxides, 1,3a,4,9b-tetrahydrochromeno-[3,4-b]-pyrroles, or 1,2,3,3a,4,9b-hexahydrochromeno-[3,4-b]-pyrroles in good yields without changing the relative configuration of the pyran ring. A similar process involving the 2-CCl3-substituted 3-nitro-4-phenacylchromanes is accompanied by reductive dehalogenation to form the corresponding 4-dichloromethyl-substituted fused chromanes along with the 3-(2-hydroxyaryl)-2-(2,2-dichlorovinyl)-5-phenyl-2H-pyrroline 1-oxides as pyran ring opening products. The structure and relative configuration of the obtained products was reliably confirmed by X-ray diffraction analysis and 2D NMR spectroscopy.",

author = "Vladislav Korotaev and Igor Kutyashev and Maxim Sannikov and Mishchenko, {Maria A.} and Zavyalova, {Lyudmila S.} and Ivan Kochnev and Alexey Barkov and Nikolay Zimnitskiy and Vyacheslav Sosnovskikh",

note = "The work was financially supported by the Russian Foundation for Basic Research (grant 20-03-00716) and the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2023-0016). Analytical studies were carried out using equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch) and Centre for Joint Use “Laboratory of Complex Investigations and Expert Evaluation of Organic Materials” at the Ural Federal University.",

year = "2024",

doi = "10.1021/acs.joc.3c02191",

language = "English",

volume = "89",

pages = "1567--1590",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

}

RIS

TY - JOUR

T1 - Tunable Zinc-Mediated Reductive Cyclization of Diastereomeric 3-Nitro-4-phenacyl-2-(trihalomethyl)chromanes to Fused Pyrroline N-Oxides, Pyrrolines, and Pyrrolidines

AU - Korotaev, Vladislav

AU - Kutyashev, Igor

AU - Sannikov, Maxim

AU - Mishchenko, Maria A.

AU - Zavyalova, Lyudmila S.

AU - Kochnev, Ivan

AU - Barkov, Alexey

AU - Zimnitskiy, Nikolay

AU - Sosnovskikh, Vyacheslav

N1 - The work was financially supported by the Russian Foundation for Basic Research (grant 20-03-00716) and the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2023-0016). Analytical studies were carried out using equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch) and Centre for Joint Use “Laboratory of Complex Investigations and Expert Evaluation of Organic Materials” at the Ural Federal University.

PY - 2024

Y1 - 2024

N2 - Reductive cyclization of trans,trans- and trans,cis-isomers of the 2-CF3-substituted 3-nitro-4-phenacylchromanes with Zn-based reductive systems, depending on the conditions, affords 4-CF3-substituted 1,3a,4,9b-tetrahydrochromeno-[3,4-b]-pyrrole 3-oxides, 1,3a,4,9b-tetrahydrochromeno-[3,4-b]-pyrroles, or 1,2,3,3a,4,9b-hexahydrochromeno-[3,4-b]-pyrroles in good yields without changing the relative configuration of the pyran ring. A similar process involving the 2-CCl3-substituted 3-nitro-4-phenacylchromanes is accompanied by reductive dehalogenation to form the corresponding 4-dichloromethyl-substituted fused chromanes along with the 3-(2-hydroxyaryl)-2-(2,2-dichlorovinyl)-5-phenyl-2H-pyrroline 1-oxides as pyran ring opening products. The structure and relative configuration of the obtained products was reliably confirmed by X-ray diffraction analysis and 2D NMR spectroscopy.

AB - Reductive cyclization of trans,trans- and trans,cis-isomers of the 2-CF3-substituted 3-nitro-4-phenacylchromanes with Zn-based reductive systems, depending on the conditions, affords 4-CF3-substituted 1,3a,4,9b-tetrahydrochromeno-[3,4-b]-pyrrole 3-oxides, 1,3a,4,9b-tetrahydrochromeno-[3,4-b]-pyrroles, or 1,2,3,3a,4,9b-hexahydrochromeno-[3,4-b]-pyrroles in good yields without changing the relative configuration of the pyran ring. A similar process involving the 2-CCl3-substituted 3-nitro-4-phenacylchromanes is accompanied by reductive dehalogenation to form the corresponding 4-dichloromethyl-substituted fused chromanes along with the 3-(2-hydroxyaryl)-2-(2,2-dichlorovinyl)-5-phenyl-2H-pyrroline 1-oxides as pyran ring opening products. The structure and relative configuration of the obtained products was reliably confirmed by X-ray diffraction analysis and 2D NMR spectroscopy.

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001157576900001

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85183137771

U2 - 10.1021/acs.joc.3c02191

DO - 10.1021/acs.joc.3c02191

M3 - Article

VL - 89

SP - 1567

EP - 1590

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -

ID: 52509508