Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
J Org Chem. 2022 Jan 21;87(2):1537-1540. doi: 10.1021/acs.joc.1c02456. Epub 2022 Jan 10.
An unusual type of highly reactive sultam-based dicarboxylic acids and correscponding anhydrides was employed in the Castagnoli-Cushman reaction delivering diastereomerically pure adducts at room temperature. Due to steric congestion, the initial adducts were prone to decarboxylation affording diastereomeric mixtures of bicyclic sultam lactams, separable by HPLC. The choice of a protecting group on the sultam nitrogen atom allows liberation of the -sultam, which is not only suitable for further modification but represents a known pharmacophore for carbonic anhydrase inhibition.
一种不寻常的高反应性琥珀酰亚胺基二羧酸及其相应的酸酐被用于 Castagnoli-Cushman 反应，在室温下以非对映异构体纯的加合物形式得到。由于空间拥挤，初始加合物易于脱羧，得到可通过 HPLC 分离的双环琥珀酰亚胺内酰胺的非对映异构体混合物。在琥珀酰亚胺氮原子上选择保护基允许释放 - 琥珀酰亚胺，它不仅适合进一步修饰，而且代表碳酸酐酶抑制的已知药效团。
