β-和 δ-内酰胺合成中的二羧酸单酯。

Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, Russia.

Institute of Living Systems, Immanuel Kant Baltic Federal University, 236041 Kaliningrad, Russia.

Molecules. 2022 Apr 11;27(8):2469. doi: 10.3390/molecules27082469.

A -(2-methoxy-2-oxoethyl)--(phenylsulfonyl)glycine monomethyl ester of the respective dicarboxylic acid was involved in a reaction with imines promoted by acetic anhydride at an elevated temperature. Instead of the initially expected δ-lactam products of the Castagnoli-Cushman-type reaction, medicinally important 3-amino-2-azetidinones were obtained as the result of cyclization, involving a methylene group adjacent to an acid moiety. In contrast, replacing alcohol residue with hexafluoroisopropyl in the same substrate made another methylene group (adjacent to the ester moiety) more reactive to furnishing the desired δ-lactam in the Castagnoli-Cushman fashion.

一种相应的二酸的 -(2-甲氧基-2-氧代乙基）-（苯磺酰基）甘氨酸单甲酯与亚胺在醋酸酐的促进下在高温下发生反应。取代最初预期的 Castagnoli-Cushman 型反应的 δ-内酰胺产物，通过环化得到具有重要医学意义的 3-氨基-2-氮杂环丁酮，其中涉及到与酸部分相邻的亚甲基。相比之下，在相同的底物中用全氟异丙基取代醇残基，使另一个亚甲基（与酯部分相邻）更具反应性，以按照 Castagnoli-Cushman 方式提供所需的 δ-内酰胺。