Published as part of the Special Topic Recent Advances in Amide Bond Formation

Abstract

A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: α-hydroxy, α-oxy, and α-oxo amides. K₂CO₃ efficiently promotes the solvolysis of α-acetoxy amides to form α-hydroxy amides in methanol. 2-Acetoxy-2-(2-alkynyl­quinolin-3-yl)acetamides in basic methanol are cyclized to 1,3-dihydrofuro[3,4-b]quinoline-1-carboxamides via deacetylation and 5-exo-dig cyclization. Treatment of 2-hydroxy-2-[2-(phenylethynyl)quinolin-3-yl]acetamides with I₂ in basic media produces pyrrolo[2,3-b]quinoline-2,3-diones. This cyclization involves intramolecular cyclization, dealkynylative aromatization, and oxidation of the secondary alcohol.

中文翻译：

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通过Passerini缩合转化高效合成α-羟基，α-Oxy和α-Oxo酰胺

作为特别主题的一部分发表，酰胺键形成的最新进展

抽象

Passerini后缩合转化可用于合成三种类型的酰胺：α-羟基，α-氧基和α-氧代酰胺。K ₂ CO ₃有效地促进α-乙酰氧基酰胺的溶剂分解以在甲醇中形成α-羟基酰胺。碱性甲醇中的2-乙酰氧基-2-（2-炔基喹啉-3-基）乙酰胺通过脱乙酰基作用和5- exo - dig环化作用环化为1,3-二氢呋喃[3,4- b ]喹啉-1-羧酰胺。在碱性介质中用I ₂处理2-羟基-2- [2-（苯基乙炔基）喹啉-3-基]乙酰胺产生吡咯并[2,3- b]喹啉-2,3-二酮。该环化涉及分子内环化，脱炔基芳构化和仲醇的氧化。