Synthesis of Selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and Their C-H Activation

In Hui Choi; Hitesh B. Jalani; Jin Hyun Jeong

doi:10.1055/a-1296-8835

Synthesis of Selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and Their C-H Activation

In Hui Choi, Hitesh B. Jalani, Jin Hyun Jeong

Department of Pharmacy

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

2 Citations (Scopus)

Abstract

We disclose the synthesis of selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and their aryl derivatives for the first time by using selenopyran ring formation via an in situ-generated selenide that reacts directly with α-halo-β-ynone-bearing substituted pyrazoles to provide the corresponding selenopyrano[2,3- c ]pyrazol-4(1 H)-ones. Subsequent direct C-H arylation of the latter compounds effected by palladium-catalyzed Heck reactions permits the incorporation of arene substituents onto the selenopyrano[2,3- c ]pyrazol-4(1 H)-ones scaffolds with moderate to good yields, and might be useful for biological screenings.

Original language	English
Pages (from-to)	321-325
Number of pages	5
Journal	Synlett
Volume	32
Issue number	3
DOIs	https://doi.org/10.1055/a-1296-8835
Publication status	Published - 2021 Feb 12

Bibliographical note

Funding Information:
This work was carried out as a co-operative project ‘Enhancement of Korea Chemical Bank (SI1807)’ financially supported by the Korea Research Institute of Chemical Technology (KRICT) and the Yonsei Institute of Pharmaceutical Sciences.KoeaReseachInstueofChemical TechnologySI1807)

Publisher Copyright:
© 2021 Georg Thieme Verlag. All rights reserved.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Synthesis of Selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and Their C-H Activation",

abstract = "We disclose the synthesis of selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and their aryl derivatives for the first time by using selenopyran ring formation via an in situ-generated selenide that reacts directly with α-halo-β-ynone-bearing substituted pyrazoles to provide the corresponding selenopyrano[2,3- c ]pyrazol-4(1 H)-ones. Subsequent direct C-H arylation of the latter compounds effected by palladium-catalyzed Heck reactions permits the incorporation of arene substituents onto the selenopyrano[2,3- c ]pyrazol-4(1 H)-ones scaffolds with moderate to good yields, and might be useful for biological screenings.",

author = "Choi, {In Hui} and Jalani, {Hitesh B.} and Jeong, {Jin Hyun}",

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AU - Choi, In Hui

AU - Jalani, Hitesh B.

AU - Jeong, Jin Hyun

N1 - Funding Information: This work was carried out as a co-operative project ‘Enhancement of Korea Chemical Bank (SI1807)’ financially supported by the Korea Research Institute of Chemical Technology (KRICT) and the Yonsei Institute of Pharmaceutical Sciences.KoeaReseachInstueofChemical TechnologySI1807) Publisher Copyright: © 2021 Georg Thieme Verlag. All rights reserved.

PY - 2021/2/12

Y1 - 2021/2/12

N2 - We disclose the synthesis of selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and their aryl derivatives for the first time by using selenopyran ring formation via an in situ-generated selenide that reacts directly with α-halo-β-ynone-bearing substituted pyrazoles to provide the corresponding selenopyrano[2,3- c ]pyrazol-4(1 H)-ones. Subsequent direct C-H arylation of the latter compounds effected by palladium-catalyzed Heck reactions permits the incorporation of arene substituents onto the selenopyrano[2,3- c ]pyrazol-4(1 H)-ones scaffolds with moderate to good yields, and might be useful for biological screenings.

AB - We disclose the synthesis of selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and their aryl derivatives for the first time by using selenopyran ring formation via an in situ-generated selenide that reacts directly with α-halo-β-ynone-bearing substituted pyrazoles to provide the corresponding selenopyrano[2,3- c ]pyrazol-4(1 H)-ones. Subsequent direct C-H arylation of the latter compounds effected by palladium-catalyzed Heck reactions permits the incorporation of arene substituents onto the selenopyrano[2,3- c ]pyrazol-4(1 H)-ones scaffolds with moderate to good yields, and might be useful for biological screenings.

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JF - Synlett

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ER -

Synthesis of Selenopyrano[2,3- c ]pyrazol-4(1 H)-ones and Their C-H Activation

Abstract

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