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以7-甲氧基-4,4a,5,6,8a-五氢-1,2-苯并口恶嗪-3-羧酸乙酯(1a)为起始原料,经NaOH醇溶液和酸化处理,再通过二甲基氨基吡啶(DMAP)催化、1,3-双环己基碳二亚胺(DCC)脱水与7,8-二甲氧基-3-羟基-2(1氢)-喹诺酮(2)的酯化反应,成功合成了天然产物Penicilliazine的类似物P-1,总收率为54.4%,用1HNMR、13CNMR、MS和元素分析等对P-1进行了结构表征;对DCC投料量等反应条件进行了初步优化;对水解反应过程的研究发现,烯醇醚结构的化合物1a可水解失去甲基得到酮式结构的化合物7-羰基-4,4a,5,6,8,8a-六氢-1,2-苯并口恶嗪-3-羧酸(1c),而使用酮式结构1c的乙酯,未发现相应酮式结构羧酸1c的生成。
Starting from ethyl 7-methoxy-4,4a, 5,6,8a-pentahydro-1,2-benzoxazine-3-carboxylate (1a), ethanolic NaOH and acidification , And then dehydrated by 1,3-dicyclohexylcarbodiimide (DCC) catalyzed by dimethylaminopyridine (DMAP) with 7,8-dimethoxy-3-hydroxy- ), The analogue P-1 of natural product Penicilliazine was successfully synthesized. The total yield was 54.4%. The structure of P-1 was characterized by 1HNMR, 13CNMR, MS and elemental analysis. The reaction conditions were preliminarily optimized. The study on the hydrolysis reaction showed that the compound 1a with enol ether structure could hydrolyze and lose the methyl group to obtain the compound 7-carbonyl-4,4a, 5,6,8,8a-hexa Hydro-1,2-benzoxazine-3-carboxylic acid (1c), but using the ethyl ester of ketone structure 1c, no formation of the corresponding keto structure carboxylic acid 1c was found.