Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N -Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Yuan Zhao Ji; Hui Jing Li; Ying Liu; Yan Chao Wu

doi:10.1055/s-0039-1690712

Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N -Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Yuan Zhao Ji
, Hui Jing Li^*
, Ying Liu
, Yan Chao Wu

^*Corresponding author for this work

School of Marine Science and Technology, Harbin Institute of Technology Weihai
Weihai Institute of Marine Biomedical Industrial Technology

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

7 Scopus citations

Abstract

It has been reported previously that treatment of arylketone-derived arylsulfonylhydrazones with NXS/(n Bu) ₄ NX affords exclusively vinyl halides. In contrast, we have found that treatment of arylaldehyde-derived arylsulfonylhydrazones with N -chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.

Original language	English
Article number	ss-2019-h0398-op
Pages (from-to)	69-74
Number of pages	6
Journal	Synthesis (Germany)
Volume	52
Issue number	1
DOIs	https://doi.org/10.1055/s-0039-1690712
State	Published - 12 Dec 2019
Externally published	Yes

Keywords

1,2,4,5-tetrazines
N -chlorosuccinimide
chlorination
hydrazones
metal-free

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10.1055/s-0039-1690712

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title = "Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N -Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives",

abstract = "It has been reported previously that treatment of arylketone-derived arylsulfonylhydrazones with NXS/(n Bu) 4 NX affords exclusively vinyl halides. In contrast, we have found that treatment of arylaldehyde-derived arylsulfonylhydrazones with N -chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.",

keywords = "1,2,4,5-tetrazines, N -chlorosuccinimide, chlorination, hydrazones, metal-free",

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doi = "10.1055/s-0039-1690712",

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T1 - Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N -Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

AU - Ji, Yuan Zhao

AU - Li, Hui Jing

AU - Liu, Ying

AU - Wu, Yan Chao

PY - 2019/12/12

Y1 - 2019/12/12

N2 - It has been reported previously that treatment of arylketone-derived arylsulfonylhydrazones with NXS/(n Bu) 4 NX affords exclusively vinyl halides. In contrast, we have found that treatment of arylaldehyde-derived arylsulfonylhydrazones with N -chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.

AB - It has been reported previously that treatment of arylketone-derived arylsulfonylhydrazones with NXS/(n Bu) 4 NX affords exclusively vinyl halides. In contrast, we have found that treatment of arylaldehyde-derived arylsulfonylhydrazones with N -chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.

KW - 1,2,4,5-tetrazines

KW - N -chlorosuccinimide

KW - chlorination

KW - hydrazones

KW - metal-free

UR - https://www.scopus.com/pages/publications/85076682766

U2 - 10.1055/s-0039-1690712

DO - 10.1055/s-0039-1690712

M3 - 文章

AN - SCOPUS:85076682766

SN - 0039-7881

VL - 52

SP - 69

EP - 74

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 1

M1 - ss-2019-h0398-op

ER -

Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N -Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Abstract

Keywords

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