Abstract

The alkylation of 3-hyroxycycloalka[c]- and 6-hydroxypyrano[3,4-c]pyridines with ethyl chloroacetate and ethyl 4-chlorobutanoate gave the corresponding oxy esters which were converted to amides by reaction with various amines. The synthesized acetamide derivatives underwent base-catalyzed Smiles type rearrangement to 3-aminotetrahydroquinolines or intramolecular cyclization to 1-aminofuro[2,3-b]isoquinolines, depending on the substituents on the amide nitrogen atom. Butanamide derivatives failed to react under similar conditions.

中文翻译：

---

环烷基[c]-和吡喃并[3,4-c]吡啶衍生的含氧酰胺的合成与转化

摘要

3-羟氧基环烷基[ c ] -和6-羟基吡喃并[3，4- c ]吡啶与氯乙酸乙酯和4-氯丁酸乙酯的烷基化反应得到相应的氧基酯，通过与各种胺反应将其转化为酰胺。合成的乙酰胺衍生物根据酰胺氮原子上的取代基进行了碱催化的Smiles型重排成3-氨基四氢喹啉或分子内环化成1-氨基呋喃[2,3- b ]异喹啉。丁酰胺衍生物在相似条件下无法反应。