Synlett

An Original One-Pot Synthesis of Dialkyl-Substituted Anthraquinones

P Vanelle, T Terme, J Maldonado, MP Crozet…

Index: Vanelle, Patrice; Terme, Thierry; Maldonado, Jose; Crozet, Michel P.; Giraud, Luc Synlett, 1998 , # 10 p. 1067 - 1068

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Citation Number: 2

Abstract

Abstract: 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 ...