, volume 23 , issue 16 , pages 6578-6582

Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines

Xianjun Xu ¹

Huangdi Feng ²

Nandini Sharma ^{1, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven B-3001, Belgium |

College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, People’s Republic of China |

Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, Moscow 117198, Russia |

Publication type: Journal Article

Publication date: 2021-08-11

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.1c02416

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PubMed ID: 34379418

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

An efficient palladium-catalyzed reaction of N-propargyl oxazolidines for the construction of 4-substituted isoquinolines under microwave irradiation is developed. This transformation proceeds through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade via C-O and C-N bond cleavages of the oxazolidine ring. The practical value of this method has also been explored by conducting a millimole-scale reaction, as well as by transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.

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Xu X. et al. Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines // Organic Letters. 2021. Vol. 23. No. 16. pp. 6578-6582.

GOST all authors (up to 50) Copy

Xu X., Feng H., Sharma N. Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines // Organic Letters. 2021. Vol. 23. No. 16. pp. 6578-6582.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.1c02416

UR - https://doi.org/10.1021/acs.orglett.1c02416

TI - Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines

T2 - Organic Letters

AU - Xu, Xianjun

AU - Feng, Huangdi

AU - Sharma, Nandini

PY - 2021

DA - 2021/08/11

PB - American Chemical Society (ACS)

SP - 6578-6582

IS - 16

VL - 23

PMID - 34379418

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Xu,

author = {Xianjun Xu and Huangdi Feng and Nandini Sharma},

title = {Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines},

journal = {Organic Letters},

year = {2021},

volume = {23},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/acs.orglett.1c02416},

number = {16},

pages = {6578--6582},

doi = {10.1021/acs.orglett.1c02416}

}

MLA

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MLA Copy

Xu, Xianjun, et al. “Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines.” Organic Letters, vol. 23, no. 16, Aug. 2021, pp. 6578-6582. https://doi.org/10.1021/acs.orglett.1c02416.

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)