Lepikhina Anastasia, Dar'in Dmitry, Bakulina Olga, Chupakhin Evgeny, Krasavin Mikhail
Saint Petersburg State University , Saint Petersburg, 199034 Russian Federation.
Immanuel Kant Baltic Federal University , Kaliningrad, 236016 Russian Federation.
ACS Comb Sci. 2017 Nov 13;19(11):702-707. doi: 10.1021/acscombsci.7b00118. Epub 2017 Oct 26.
A new format for the Castagnoli-Cushman reaction of structurally diverse dicarboxylic acids, amines, and aldehydes in the presence of acetic anhydride as dehydrating agent is described. The reaction is distinctly amenable to parallel format: the combinatorial array of 180 reactions delivered 157 products of >85% purity without chromatographic purification (of this number, 143 compounds had >94% purity). The new method offers a convenient preparation of the skeletally and peripherally diverse, lead- and druglike γ- and δ-lactam carboxylic acids with high diastereoselectivity in combinatorial fashion.
本文描述了一种新的Castagnoli-Cushman反应形式，该反应在乙酸酐作为脱水剂的存在下，使结构多样的二元羧酸、胺和醛发生反应。该反应明显适用于平行反应形式：180个反应的组合阵列产生了157种纯度>85%的产物，无需色谱纯化（其中，143种化合物的纯度>94%）。这种新方法以组合方式提供了一种方便的制备方法，可用于合成骨架和外围结构多样、具有先导物和药物样性质的γ-和δ-内酰胺羧酸，且具有高非对映选择性。
