Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

Kai Qiao; Li Wan; Xiaoning Sun; Kai Zhang; Ning Zhu; Xin Li; Kai Guo

doi:10.1002/ejoc.201501567

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh₃/Cl₃CCN

Kai Qiao, Li Wan, Xiaoning Sun, Kai Zhang, Ning Zhu, Xin Li, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

35 Scopus citations

Abstract

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh₃/Cl₃CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

Original language	English
Pages (from-to)	1606-1611
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.201501567
State	Published - 1 Mar 2016

Keywords

Halogenation
Nitrogen heterocycles
Nitrogen oxides
Phosphanes
Regioselectivity
Synthetic methods

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10.1002/ejoc.201501567

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title = "Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN",

abstract = "A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.",

keywords = "Halogenation, Nitrogen heterocycles, Nitrogen oxides, Phosphanes, Regioselectivity, Synthetic methods",

author = "Kai Qiao and Li Wan and Xiaoning Sun and Kai Zhang and Ning Zhu and Xin Li and Kai Guo",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

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TY - JOUR

T1 - Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

AU - Qiao, Kai

AU - Wan, Li

AU - Sun, Xiaoning

AU - Zhang, Kai

AU - Zhu, Ning

AU - Li, Xin

AU - Guo, Kai

PY - 2016/3/1

Y1 - 2016/3/1

N2 - A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

AB - A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

KW - Halogenation

KW - Nitrogen heterocycles

KW - Nitrogen oxides

KW - Phosphanes

KW - Regioselectivity

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84959084127&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201501567

DO - 10.1002/ejoc.201501567

M3 - 文章

AN - SCOPUS:84959084127

SN - 1434-193X

VL - 2016

SP - 1606

EP - 1611

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 8

ER -

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh₃/Cl₃CCN

Abstract

Keywords

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