Fu‐She Han, G. Ling, Jing Zhang
2018
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Heterocycles
Abstract
The design and synthesis of a novel type of macrocyclic compounds containing indole and 1,4-dihydropyridine heterocyclic subunits is presented. The key reaction involved in the synthesis was a base-mediated dimerization of [2-(1H-indol-3-yl)ethyl]pyridinium salts. The structure of the macrocycles was unambiguously confirmed by NMR and HRMS spectroscopic and X-ray single crystal diffraction. INTRODUCTION The design and synthesis of heteroarene-based macromolecules possessing defined structural architectures are the focus of intense research in the area of molecular and ion recognition,1 supramolecular chemistry,2 and drug design.3 In this regard, the nitrogen containing heterocycles such as pyridine and pyrrole,4 thiazoline and thiazole,5 and oxazole and oxazoline6 have been preferentially selected as fundamental subunits since these classess of subunits may participate in a wide varieties of non-covalent interactions, such as dipole–dipole and interactions, hydrogen-bonding, and chelation. On the other hand, the indole nucleus are prevailing structural motifs in natural products and synthetic molecules for pharmaceuticals and materials.7 However, to our knowledge, the indole skeleton has been rarely considered as a useful substructure for the fabrication of macrocycles Previously, we and others have designed and synthesized a variety of thiazoline/thiazoleand oxazole-based macrocycles5,6 (Figure 1), and have investigated the recognition property of some of these macrocycles serving as host compounds toward small organic molecules or metal ions. With the aim of HETEROCYCLES, Vol. 96, No. 1, 2018 67