分子内酰基化反应合成新型六环稠杂环化合物

Synthesis of Novel Hexacyclic-fused Heterocyclic Compounds via Intramolecular Friedel-Crafts Acylation

以2-氯甲基-3-苯并喹啉甲酸乙酯(1)为底物与α-萘酚、β-萘酚反应经"一锅法"合成了中间体2-(α-萘氧甲基)苯并[h]喹啉-3-羧酸(2a)、2-(β-萘氧甲基)苯并[H]喹啉-3-羧酸(2b).化合物2a,2b在Eaton's试剂作用下合成两种新型六环稠杂环化合物萘并[2',1',6,7]氧杂卓并[3,4-b]苯并喹啉-7(14H)-酮(3a)和萘并[1',2',6,7]氧杂卓并[3,4-b]苯并喹啉-15(8H)-酮(3b).化合物2a,2b发生分子内傅一克酰基化闭环反应,所合成的新化合物2a、2b、3a、3b的结构经红外光谱、核磁共振谱、质谱及元素分析等得以确认.

The hitherto unreported benzo[h]naphtho[1′,2′,6,7]oxepino[3,4-b] quinolin-17（8H） -one （3a） was synthesized by the intramolecular Friedel -Crafts acylation reaction of 2 -（（ naphthalen -2 -yloxy）methyl）benzo[h]quinoline -3-carboxylic acid 2 under the treatment of Eaton′s reagent （P2O5 -Me-SO3 ） .The precursor 2 was prepared through one -pot reaction of ethyl 2-（ chloromethyl ） benzo [ h] quinoline-3-carboxylate 1 with α-naphthol or β-naphthol .The substrate 1 was obtained in good yield by a mild , effi-cient and direct reaction of α-naphthylamine with 4 -chloroacetoacetate under the treatment of Vilsmeier -Haack reagent.The structures of all the new compounds were identified by ESI -MS, IR, NMR spectra and Ele-mental analysis .