Download PDF
Synlett 1998; 1998(10): 1067-1068
DOI: 10.1055/s-1998-1863
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >