Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF3-Substituted β-Aza-spiroindolines and β-Carbolines

Luo-Rong Yuan; You Zi; Shun-Jun Ji; Xiao-Ping Xu

doi:10.1021/acs.joc.4c02302

Radical-Initiated Dearomative Annulation of Tryptamine-Derived Isocyanides: Selective Synthesis of CF₃-Substituted β-Aza-spiroindolines and β-Carbolines

J Org Chem. 2024 Nov 1;89(21):15979-15989. doi: 10.1021/acs.joc.4c02302. Epub 2024 Oct 22.

Authors

Luo-Rong Yuan¹, You Zi², Shun-Jun Ji¹, Xiao-Ping Xu^{1

3}

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. China.
² School of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. China.
³ Innovation Center for Chemical Science, Soochow University, Suzhou 215123, P. R. China.

PMID: 39436351
DOI: 10.1021/acs.joc.4c02302

Abstract

A mild approach for synthesizing CF₃-substituted β-aza-spiroindolines and β-carbolines from tryptamine-derived isocyanides via site-selective radical annulations has been reported. The crucial role of C2 substituents in the selective annulation process has been clarified. The approach shows good generality and practical applicability, highlighting its effectiveness and versatility.