关键词: 分子内关环, 一步反应, 多取代芳香二酯

Abstract: Substituted 2,7-naphthalene dicarboxylates, possessing heat-resistant property, and giving print ink with good a abrasion resistance and adhesion to various papers, have been found to be extremely useful in polymer industry. Herein, we report a straightforward synthesis of polysubstituted diethyl 2,7-naphthalenedicarboxylates from the readily prepared diethyl 2-methoxy-4,6-dimethyl-1,3-benzene dicarboxylate(1). The tandem Micheal addition-cyclization of benzene diester yielded the substituted 1,2,3,4-tetrahydro-nathtalene-1-one(2). This is a novel and efficient route for the cyclization of aromatic ester onto cyclohexanone or phenolic ring. Substituted 1-naphthols(4) were obtained by a sequential bromination and deprotonation of the compound(2). The aromatization of compound(3) couldn′t be executed by the general route. Herein, the use of DBU is extremely efficient. The methylation of the naphtol(4) generated a symmetric substituted naphthalene dicarboxylate(5b). The structures of all compounds(2a-5b) were characterized by ¹H NMR, ¹³C NMR, IR, MS and elemental analysis. They are unknown compounds.

Key words: Intramolecular cyclization, One pot reaction, Polystituted aromatic diesters