通过金（I）催化的 -炔基喹唑酮连接的吲哚的去芳构化环化反应合成螺吲哚啉-3,3'-吡咯并[2,1-]喹唑啉酮。

Synthesis of spiroindolenine-3,3'-pyrrolo[2,1-]quinazolinones through gold(I)-catalyzed dearomative cyclization of -alkynyl quinazolinone-tethered indoles.

机构信息

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin, 541004, China.

出版信息

Org Biomol Chem. 2022 Mar 9;20(10):2069-2074. doi: 10.1039/d1ob02492b.

DOI:10.1039/d1ob02492b

PMID:35201247

Abstract

A variety of functionalized spiroindolenine-3,3'-pyrrolo[2,1-]quinazolinones were prepared in good to excellent yields through a gold(I)-catalyzed dearomative cyclization of -alkynyl quinazolinone-tethered C2-substituted indoles. This reaction features a broad substrate scope, good functional group tolerance, and easy gram-scale preparation and transformations. Furthermore, biological activity studies showed that most of the obtained spiroindolenine-3,3'-pyrrolo[2,1-]quinazolinone scaffolds showed potential as good anti-inflammatory agents.

摘要

通过金（I）催化的-炔基喹唑酮-连接的 C2-取代吲哚的去芳构化环化反应，以良好到优异的收率制备了各种功能化的螺吲哚啉-3,3'-吡咯并[2,1-]喹唑啉酮。该反应具有广泛的底物范围、良好的官能团耐受性以及易于进行克级规模的制备和转化。此外，生物活性研究表明，大多数获得的螺吲哚啉-3,3'-吡咯并[2,1-]喹唑啉酮骨架作为潜在的良好抗炎剂。