Selective C-O Bond Forming Reactions at Indole-C2-Position toward Polycyclic Indolone or Indolinone Derivatives Tethered with Medium-Sized Rings

Zongkang Wang; Liqiang Yin; Mengdan Wang; Yilin Zhu; Yajie Yang; Lu Cheng; Chengyu Wang; Yanzhong Li

doi:10.1021/acs.orglett.2c02398

Selective C-O Bond Forming Reactions at Indole-C2-Position toward Polycyclic Indolone or Indolinone Derivatives Tethered with Medium-Sized Rings

Org Lett. 2022 Sep 2;24(34):6272-6276. doi: 10.1021/acs.orglett.2c02398. Epub 2022 Aug 18.

Authors

Zongkang Wang¹, Liqiang Yin¹, Mengdan Wang¹, Yilin Zhu¹, Yajie Yang¹, Lu Cheng¹, Chengyu Wang², Yanzhong Li^{1

3}

Affiliations

¹ School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai, 200241, China.
² School of Chemistry and Chemical Engineering, Linyi University, Shuangling Road, Linyi, Shandong 276000, China.
³ Key Laboratory of Polar Materials and Devices, Ministry of Education, East China Normal University, Shanghai 200062, China.

PMID: 35980745
DOI: 10.1021/acs.orglett.2c02398

Abstract

A methodology involving the chemoselective synthesis of tetracyclic [1,3]oxazino[3,2-a]indol-4-one or tetracyclic [1,3]oxazino[3,2-a]indoline-4-one tethered with a medium-sized ring by cross dehydrogenative coupling (CDC) or nucleophilic addition (NA) reaction has been developed. [1,3]Oxazino[3,2-a]indol-4-one compounds fused with a medium-sized ring were constructed through a CDC reaction in the presence of I₂ and K₂CO₃. Whereas, [1,3]oxazino[3,2-a]indoline-4-ones tethered with a medium-sized ring were obtained with a TfOH system by NA reaction.