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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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

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10.1016/j.tetlet.2009.06.107