新型多取代2,7-萘二甲酸二乙酯的合成

Synthesis of Novel Polysubstituted Diethyl 2,7-Naphthalene Dicarboxylates

以 4 ,6 -二甲基 -2 -甲氧基 -1 ,3-苯二甲酸二乙酯为原料 ,经 Micheal加成、环化、溴化、消除等 5步反应 ,合成新型的多取代 2 ,7-萘二甲酸二乙酯 .该合成路线步骤少 ,收率高 ,反应条件温和 .产物中的 4个新化合物的结构均经元素分析、核磁共振、红外光谱和质谱确证 .

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.