Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-03-21 , DOI: 10.1016/j.tetlet.2018.03.061 Irina R. Knyazeva , Karina M. Mukhamedyanova , Victor V. Syakaev , Aidar T. Gubaidullin , Wolf D. Habicher , Alexander R. Burilov
Novel calix[4]resorcinols containing four triazole fragments on the aromatic substituents of the calixarene framework were synthesized via a one-step condensation of resorcinol and its derivatives with 4-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)benzaldehyde. The macrocyclic products are rctt- and/or rccc-isomers, which were isolated and characterized by NMR and single crystal X-ray diffraction studies. The same products were also prepared via the click-reaction of benzyl azide with previously synthesized calix[4]resorcinols containing four alkyne terminal groups on the aromatic substituents. In this case, only rctt-diastereomers of the corresponding calixarenes were isolated, which is governed by conformational features of the starting macrocycles.
中文翻译:
新型含三唑杯[4]间苯二酚的rccc-和rctt-非对映异构体的合成
通过间苯二酚及其衍生物与4-(1-苄基-1 H- [1,2,3]三唑-4-基甲氧基)苯甲醛。大环产物是rctt-和/或rccc-异构体,通过NMR和单晶X射线衍射研究对其进行了分离和表征。通过苄基叠氮化物与先前合成的杯芳烃[4]间苯二酚的点击反应也制备了相同的产物,杯芳烃[4]间苯二酚在芳族取代基上包含四个炔烃末端基团。在这种情况下,只有rctt分离出相应杯芳烃的β-非对映异构体,其受起始大环的构象特征支配。