Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions

Deepak Kumar Barange; Veerababurao Kavala; B. Rama Raju; Chun Wei Kuo; Chi Tseng; Yu Chen Tu; Ching-Fa Yao

doi:10.1016/j.tetlet.2009.06.107

Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions

Deepak Kumar Barange, Veerababurao Kavala, B. Rama Raju, Chun Wei Kuo, Chi Tseng, Yu Chen Tu, Ching-Fa Yao

Department of Chemistry

Research output: Contribution to journal › Article

24 Citations (Scopus)

Abstract

C-Alkylation of 2-hydroxy-1,4-naphthoquinone to various nitroolefins was achieved under catalyst-free employing 'on water' conditions. The mechanism for the formation can be explained on the basis of dual activation of nitroalkene and 2-hydroxy-1,4-naphthoquinones via hydrogen bonding. Simple reaction conditions, high yields of the products, and environmentally benign medium are attractive features of this method.

Original language	English
Pages (from-to)	5116-5119
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2009.06.107
Publication status	Published - 2009 Sep 9

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Alkylation

Catalysts

Water

Hydrogen Bonding

Hydrogen bonds

Chemical activation

lawsone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Barange, D. K., Kavala, V., Raju, B. R., Kuo, C. W., Tseng, C., Tu, Y. C., & Yao, C-F. (2009). Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions. Tetrahedron Letters, 50(36), 5116-5119. https://doi.org/10.1016/j.tetlet.2009.06.107

Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions. / Barange, Deepak Kumar; Kavala, Veerababurao; Raju, B. Rama; Kuo, Chun Wei; Tseng, Chi; Tu, Yu Chen; Yao, Ching-Fa.

In: Tetrahedron Letters, Vol. 50, No. 36, 09.09.2009, p. 5116-5119.

Research output: Contribution to journal › Article

Barange, DK, Kavala, V, Raju, BR, Kuo, CW, Tseng, C, Tu, YC & Yao, C-F 2009, 'Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions', Tetrahedron Letters, vol. 50, no. 36, pp. 5116-5119. https://doi.org/10.1016/j.tetlet.2009.06.107

Barange DK, Kavala V, Raju BR, Kuo CW, Tseng C, Tu YC et al. Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions. Tetrahedron Letters. 2009 Sep 9;50(36):5116-5119. https://doi.org/10.1016/j.tetlet.2009.06.107

Barange, Deepak Kumar ; Kavala, Veerababurao ; Raju, B. Rama ; Kuo, Chun Wei ; Tseng, Chi ; Tu, Yu Chen ; Yao, Ching-Fa. / Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free 'on water' conditions. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 36. pp. 5116-5119.

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10.1016/j.tetlet.2009.06.107