Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles

Mei Huey Lin, Kung Yu Liang, Chang Hsien Tsai, Yu Chun Chen, Hung Chang Hsiao, Yi Syuan Li, Chung Hao Chen, Hau Chun Wu

Research output: Contribution to journal › Article

Abstract

A procedure has been developed for synthesis of 2-alkenyl-2H-indazoles starting from 2-(2-carbonylmethyl)-2H-indazoles, which are prepared by gallium/aluminium- and aluminium-mediated, direct, regioselective alkylation of indazoles with α-bromocarbonyl compounds. The structure of 3-(2H-indazol-2-yl)-2H-chromen-2-one was proven by X-ray crystallography. The styrene- and coumarin-2H-indazoles produced by using the newmethod were found to have interesting fluorescence properties.

Original languageEnglish
Article number238
JournalMolecules
Volume21
Issue number2
DOIs
Publication statusPublished - 2016 Feb

Fingerprint

Indazoles
aluminum
alkylation
synthesis
Aluminum
styrenes
crystallography
gallium
fluorescence
Gallium
Styrene
X ray crystallography
X Ray Crystallography
Alkylation
x rays
Fluorescence

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Lin, M. H., Liang, K. Y., Tsai, C. H., Chen, Y. C., Hsiao, H. C., Li, Y. S., ... Wu, H. C. (2016). Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles. Molecules, 21(2), [238]. https://doi.org/10.3390/molecules21020238
Lin, Mei Huey ; Liang, Kung Yu ; Tsai, Chang Hsien ; Chen, Yu Chun ; Hsiao, Hung Chang ; Li, Yi Syuan ; Chen, Chung Hao ; Wu, Hau Chun. / Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles. In: Molecules. 2016 ; Vol. 21, No. 2.
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abstract = "A procedure has been developed for synthesis of 2-alkenyl-2H-indazoles starting from 2-(2-carbonylmethyl)-2H-indazoles, which are prepared by gallium/aluminium- and aluminium-mediated, direct, regioselective alkylation of indazoles with α-bromocarbonyl compounds. The structure of 3-(2H-indazol-2-yl)-2H-chromen-2-one was proven by X-ray crystallography. The styrene- and coumarin-2H-indazoles produced by using the newmethod were found to have interesting fluorescence properties.",
author = "Lin, {Mei Huey} and Liang, {Kung Yu} and Tsai, {Chang Hsien} and Chen, {Yu Chun} and Hsiao, {Hung Chang} and Li, {Yi Syuan} and Chen, {Chung Hao} and Wu, {Hau Chun}",
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Lin, MH, Liang, KY, Tsai, CH, Chen, YC, Hsiao, HC, Li, YS, Chen, CH & Wu, HC 2016, 'Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles', Molecules, vol. 21, no. 2, 238. https://doi.org/10.3390/molecules21020238

Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles. / Lin, Mei Huey; Liang, Kung Yu; Tsai, Chang Hsien; Chen, Yu Chun; Hsiao, Hung Chang; Li, Yi Syuan; Chen, Chung Hao; Wu, Hau Chun.

In: Molecules, Vol. 21, No. 2, 238, 02.2016.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles

AU - Lin, Mei Huey

AU - Liang, Kung Yu

AU - Tsai, Chang Hsien

AU - Chen, Yu Chun

AU - Hsiao, Hung Chang

AU - Li, Yi Syuan

AU - Chen, Chung Hao

AU - Wu, Hau Chun

PY - 2016/2

Y1 - 2016/2

N2 - A procedure has been developed for synthesis of 2-alkenyl-2H-indazoles starting from 2-(2-carbonylmethyl)-2H-indazoles, which are prepared by gallium/aluminium- and aluminium-mediated, direct, regioselective alkylation of indazoles with α-bromocarbonyl compounds. The structure of 3-(2H-indazol-2-yl)-2H-chromen-2-one was proven by X-ray crystallography. The styrene- and coumarin-2H-indazoles produced by using the newmethod were found to have interesting fluorescence properties.

AB - A procedure has been developed for synthesis of 2-alkenyl-2H-indazoles starting from 2-(2-carbonylmethyl)-2H-indazoles, which are prepared by gallium/aluminium- and aluminium-mediated, direct, regioselective alkylation of indazoles with α-bromocarbonyl compounds. The structure of 3-(2H-indazol-2-yl)-2H-chromen-2-one was proven by X-ray crystallography. The styrene- and coumarin-2H-indazoles produced by using the newmethod were found to have interesting fluorescence properties.

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Lin MH, Liang KY, Tsai CH, Chen YC, Hsiao HC, Li YS et al. Synthesis of 2-alkenyl-2H-indazoles from 2-(2-carbonylmethyl)-2H-indazoles. Molecules. 2016 Feb;21(2). 238. https://doi.org/10.3390/molecules21020238

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