Aksakal Nuray Esra, Zora Metin
Department of Chemistry, Faculty of Arts and Science, Middle East Technical University, 06800 Ankara, Turkey.
Department of Nutrition and Dietetics, Faculty of Health Sciences, Halic University, 34060 Istanbul, Turkey.
ACS Omega. 2024 Jul 16;9(30):33251-33260. doi: 10.1021/acsomega.4c05239. eCollection 2024 Jul 30.
In this paper, we describe an efficient InCl-catalyzed two-component reaction of 1-(2-aminophenyl)pyrroles/indoles and 2-propargyloxybenzaldehydes for the direct synthesis of 12b-benzo[6,7]1,4-oxazepino[4,5-]pyrrolo/indolo[2,1-]quinoxalines. This high atom- and step-economical one-pot process generates three new C/N-C bonds in a single synthetic operation, resulting in the formation of new six- and seven-membered heterocyclic rings. The easy availability of the starting materials, the use of the relatively inexpensive indium catalyst, and the good substrate scope are the salient features of this strategy. The proposed mechanistic pathway involves imine formation, two consecutive cyclizations via electrophilic aromatic substitution and nucleophilic addition reactions, and the H shift step.
在本文中，我们描述了一种高效的InCl催化的1-(2-氨基苯基)吡咯/吲哚与2-炔丙氧基苯甲醛的双组分反应，用于直接合成12b-苯并[6,7]1,4-恶唑并[4,5-]吡咯/吲哚并[2,1-]喹喔啉。这种高原子经济性和步骤经济性的一锅法在单一合成操作中生成三个新的C/N-C键，从而形成新的六元和七元杂环。起始原料易于获得、使用相对廉价的铟催化剂以及良好的底物范围是该策略的显著特点。所提出的反应机理途径包括亚胺形成、通过亲电芳香取代和亲核加成反应的两个连续环化以及H迁移步骤。
