通过涉及β-羟基α-氨基砜的4-二甲氨基吡啶介导的串联环化反应合成苯并呋喃衍生物。

Zhu Rong-Rong, Hou Xi-Qiang, Du Da-Ming

School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No. 5 Zhongguancun South Street, Beijing 100081, China.

Key Laboratory of Medicinal Molecule Science and Pharmaceutical Technology, Ministry of Industry and Information Technology, No. 5 Zhongguancun South Street, Beijing 100081, China.

Molecules. 2024 Aug 6;29(16):3725. doi: 10.3390/molecules29163725.

An efficient cascade cyclization strategy was developed to synthesize aminobenzofuran spiroindanone and spirobarbituric acid derivatives utilizing 2-bromo-1,3-indandione, 5-bromo-1,3-dimethylbarbituric acid, and -hydroxy α-aminosulfones as substrates. Under the optimized reaction conditions, the corresponding products were obtained with high efficiency, exceeding 95% and 85% yields for the respective derivatives. This protocol demonstrates exceptional substrate versatility and robust scalability up to the Gram scale, establishing a stable platform for the synthesis of 3-aminobenzofuran derivative. The successful synthesis paves the way for further biological evaluations with potential implications in scientific research.

开发了一种高效的串联环化策略，以2-溴-1,3-茚二酮、5-溴-1,3-二甲基巴比妥酸和α-羟基α-氨基砜为底物，合成氨基苯并呋喃螺茚满二酮和螺巴比妥酸衍生物。在优化的反应条件下，高效获得了相应产物，各衍生物的产率分别超过95%和85%。该方案显示出优异的底物通用性和高达克级规模的强大可扩展性，为3-氨基苯并呋喃衍生物的合成建立了一个稳定的平台。成功的合成为此后具有科研潜在意义的生物学评估铺平了道路。