Organic Letters

, volume 23 , issue 2 , pages 358-364

Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation

Xiaoyu Yang ¹

Liang Wang ^{1, 2}

Fangzhi Hu ¹

Lubin Xu ¹

Sanming Li ³

Shuai-Shuai Li ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Changcheng Road #700, Qingdao 266109, PR China |

College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Zhengzhou Road #53, Qingdao 266042, PR China |

School of Pharmacy, Shenyang Pharmaceutical University, Hongliu Road #85, Benxi 117004, PR China |

Publication type: Journal Article

Publication date: 2020-12-23

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.0c03863

Copy DOI

PubMed ID: 33355465

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The switchable synthesis of 3-non, 3-mono, 3,3'-disubstituted 3,4-dihydroquinolin-2(1H)-ones was developed through a redox-neutral hydride-transfer/N-dealkylation/N-acylation strategy from o-aminobenzaldehyde with 4-hydroxycoumarin, and Meldrum's acid, respectively. The unprecedented strategy for the synthesis of 3,3'-highly functionalized 3,4-dihydroquinolin-2(1H)-one has been realized with the in situ utilization of the released HCHO via the o-QM involved Michael addition. In addition, the synthetic utility of this protocol has been well illustrated via concise synthesis of CYP11B2 inhibitor.

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GOST |

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Yang X. et al. Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation // Organic Letters. 2020. Vol. 23. No. 2. pp. 358-364.

GOST all authors (up to 50) Copy

Yang X., Wang L., Hu F., Xu L., Li S., Li S. Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation // Organic Letters. 2020. Vol. 23. No. 2. pp. 358-364.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.0c03863

UR - https://doi.org/10.1021/acs.orglett.0c03863

TI - Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation

T2 - Organic Letters

AU - Yang, Xiaoyu

AU - Wang, Liang

AU - Hu, Fangzhi

AU - Xu, Lubin

AU - Li, Sanming

AU - Li, Shuai-Shuai

PY - 2020

DA - 2020/12/23

PB - American Chemical Society (ACS)

SP - 358-364

IS - 2

VL - 23

PMID - 33355465

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2020_Yang,

author = {Xiaoyu Yang and Liang Wang and Fangzhi Hu and Lubin Xu and Sanming Li and Shuai-Shuai Li},

title = {Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation},

journal = {Organic Letters},

year = {2020},

volume = {23},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.orglett.0c03863},

number = {2},

pages = {358--364},

doi = {10.1021/acs.orglett.0c03863}

}

MLA

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MLA Copy

Yang, Xiaoyu, et al. “Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1H)-one Derivatives via Hydride Transfer/N-Dealkylation/N-Acylation.” Organic Letters, vol. 23, no. 2, Dec. 2020, pp. 358-364. https://doi.org/10.1021/acs.orglett.0c03863.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)