One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles
One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles
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DOI：
10.1021/acs.orglett.0c01351
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发表时间：
2020-06-05
期刊：
影响因子：
5.2
通讯作者：
Frontier, Alison J.
中科院分区：
文献类型：
--
作者：
Abdul-Rashed, Shukree;Alachouzos, Georgios;Frontier, Alison J.
描述了一种新型的无金属双环级联反应，用于构建不寻常的稠杂环体系。这个简单的协议，使两个环的顺序组装在一个锅从两个简单的前体。酸性条件促进烯炔或芳炔醇与环状半缩醛胺的缩合和分子内炔基Prins反应，以形成五元、六元或七元氧杂环戊二烯并随后形成七元或八元氮杂环戊二烯并。在这种转变中，化学复杂性随着三个新键（一个C-O，一个C-C和一个C-N）在一个合成操作中的形成而迅速产生。该策略是模块化的且相对通用的，提供了一系列独特的稠合双环支架的途径。
A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven- or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.