Michael-Aldol Double Elimination Cascade to Make Pyridines: Use of Chromone for the Synthesis of Indolizines

Dirgha Raj Joshi; Ikyon Kim

doi:10.1021/acs.joc.1c00981

Michael-Aldol Double Elimination Cascade to Make Pyridines: Use of Chromone for the Synthesis of Indolizines

Dirgha Raj Joshi, Ikyon Kim

Department of Pharmacy

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

9 Citations (Scopus)

Abstract

A domino Michael-aldol double elimination route to indolizines having two different acyl groups at the C5 and C7 positions is described where chromone is employed as a two-carbon unit for the synthesis of a pyridine moiety for the first time. Various analogues were readily accessed in good yields under metal-free and eco-friendly conditions. Further manipulation of the resulting products allowed entry to novel indolizine-heterocycle adducts, which are difficult to access by other methods.

Original language	English
Pages (from-to)	10235-10248
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	86
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.1c00981
Publication status	Published - 2021 Aug 6

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.

Publisher Copyright:
© 2021 American Chemical Society.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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abstract = "A domino Michael-aldol double elimination route to indolizines having two different acyl groups at the C5 and C7 positions is described where chromone is employed as a two-carbon unit for the synthesis of a pyridine moiety for the first time. Various analogues were readily accessed in good yields under metal-free and eco-friendly conditions. Further manipulation of the resulting products allowed entry to novel indolizine-heterocycle adducts, which are difficult to access by other methods.",

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AU - Kim, Ikyon

N1 - Funding Information: We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support. Publisher Copyright: © 2021 American Chemical Society.

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AB - A domino Michael-aldol double elimination route to indolizines having two different acyl groups at the C5 and C7 positions is described where chromone is employed as a two-carbon unit for the synthesis of a pyridine moiety for the first time. Various analogues were readily accessed in good yields under metal-free and eco-friendly conditions. Further manipulation of the resulting products allowed entry to novel indolizine-heterocycle adducts, which are difficult to access by other methods.

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Michael-Aldol Double Elimination Cascade to Make Pyridines: Use of Chromone for the Synthesis of Indolizines

Abstract

Bibliographical note

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