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Synlett 1998; 1998(10): 1067-1068
DOI: 10.1055/s-1998-1863
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An Original One-Pot Synthesis of Dialkyl-Substituted Anthraquinones

Patrice Vanelle* , Thierry Terme, José Maldonado, Michel P. Crozet, Luc Giraud
  • *Laboratoire de Chimie Organique, Faculté de Pharmacie, 27 Bd Jean Moulin, 13385 Marseille Cedex 05, France; Fax (33)04 91 79 46 77; E-mail: patrice.vanelle@pharmacie.univ-mrs.fr
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Publication Date:
31 December 2000 (online)

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2,3-Bis(chloromethyl)-1,4-naphthoquinone reacts with primary nitroalkanes in a one-pot synthesis to give a series of anthraquinones bearing two n-alkyl substituents at C-2 and C-3 in good yields. The reaction is shown to proceed by two consecutive SRN1 processes followed by base-promoted nitrous acid elimination, electrocyclic ring-closure and dehydrogenation. In comparison with the classical Diels-Alder reaction, the advantage of this route is the simplicity of starting-material preparation.

anthraquinones - bischloride - nitroalkanes - phase-transfer conditions - SRN1 reaction