Synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their C-H arylation

Choi Woo-Jin; Hitesh B. Jalani; Jin Hyun Jeong

doi:10.1002/jhet.4471

Synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their C-H arylation

Choi Woo-Jin, Hitesh B. Jalani, Jin Hyun Jeong

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

Abstract

Herein, we disclose the synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their aryl derivatives using seleno-pyran ring formation via an in situ-generated selenide reacting directly with α-halo-β-ynones of substituted indoles providing selenopyrano[2,3-b]indol-4(9H)-ones. Subsequent direct C-H arylation of the these compounds by palladium-catalyzed Heck reaction enables the incorporation of aryl substituents on the selenopyrano[2,3-b]indol-4(9H)-ones scaffolds with moderate yields. This new chemo-type incorporating an indole ring may be useful for the biological screenings.

Original language	English
Pages (from-to)	1430-1434
Number of pages	5
Journal	Journal of Heterocyclic Chemistry
Volume	59
Issue number	8
DOIs	https://doi.org/10.1002/jhet.4471
Publication status	Published - 2022 Aug

Bibliographical note

Funding Information:
This work was carried out as a co‐operation project of “Enhancement of Korea Chemical Bank (SI1807) supported by Korea Research Institute of Chemical Technology (KRICT) and Yonsei Institute of Pharmaceutical Sciences for financial support.

Publisher Copyright:
© 2022 Wiley Periodicals LLC.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1002/jhet.4471

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title = "Synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their C-H arylation",

abstract = "Herein, we disclose the synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their aryl derivatives using seleno-pyran ring formation via an in situ-generated selenide reacting directly with α-halo-β-ynones of substituted indoles providing selenopyrano[2,3-b]indol-4(9H)-ones. Subsequent direct C-H arylation of the these compounds by palladium-catalyzed Heck reaction enables the incorporation of aryl substituents on the selenopyrano[2,3-b]indol-4(9H)-ones scaffolds with moderate yields. This new chemo-type incorporating an indole ring may be useful for the biological screenings.",

author = "Choi Woo-Jin and Jalani, {Hitesh B.} and Jeong, {Jin Hyun}",

note = "Funding Information: This work was carried out as a co‐operation project of “Enhancement of Korea Chemical Bank (SI1807) supported by Korea Research Institute of Chemical Technology (KRICT) and Yonsei Institute of Pharmaceutical Sciences for financial support. Publisher Copyright: {\textcopyright} 2022 Wiley Periodicals LLC.",

year = "2022",

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doi = "10.1002/jhet.4471",

language = "English",

volume = "59",

pages = "1430--1434",

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AU - Woo-Jin, Choi

AU - Jalani, Hitesh B.

AU - Jeong, Jin Hyun

N1 - Funding Information: This work was carried out as a co‐operation project of “Enhancement of Korea Chemical Bank (SI1807) supported by Korea Research Institute of Chemical Technology (KRICT) and Yonsei Institute of Pharmaceutical Sciences for financial support. Publisher Copyright: © 2022 Wiley Periodicals LLC.

PY - 2022/8

Y1 - 2022/8

N2 - Herein, we disclose the synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their aryl derivatives using seleno-pyran ring formation via an in situ-generated selenide reacting directly with α-halo-β-ynones of substituted indoles providing selenopyrano[2,3-b]indol-4(9H)-ones. Subsequent direct C-H arylation of the these compounds by palladium-catalyzed Heck reaction enables the incorporation of aryl substituents on the selenopyrano[2,3-b]indol-4(9H)-ones scaffolds with moderate yields. This new chemo-type incorporating an indole ring may be useful for the biological screenings.

AB - Herein, we disclose the synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their aryl derivatives using seleno-pyran ring formation via an in situ-generated selenide reacting directly with α-halo-β-ynones of substituted indoles providing selenopyrano[2,3-b]indol-4(9H)-ones. Subsequent direct C-H arylation of the these compounds by palladium-catalyzed Heck reaction enables the incorporation of aryl substituents on the selenopyrano[2,3-b]indol-4(9H)-ones scaffolds with moderate yields. This new chemo-type incorporating an indole ring may be useful for the biological screenings.

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Synthesis of selenopyrano[2,3-b]indol-4(9H)-ones and their C-H arylation

Abstract

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