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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)5116-5119
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number36
DOIs
Publication statusPublished - 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

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 journalArticle

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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