TBHP/I<sub>2</sub> Synergistically Promoted Three-Component Reaction of Isatins, Amines and Methylhetarenes: Transition-Metal-Free Access to 2-Hetarylquinazolin-4(3<i>H</i>)-ones
A TBHP/I<sub>2</sub> synergistically promoted three-component reaction of readily available isatins, amines, and methylhetarenes has been established. This transition-metal-free approach provides a concise and practical pathway for the assembly of structurally novel 2-hetarylquinazolin-4(3<i>H</i>)-ones, featuring a wide substrate scope and excellent functional group tolerance. Mechanistic investigations revealed that the TBHP-mediated Baeyer-Villiger-type rearrangement of isatins and the I<sub>2</sub>-promoted sp<sup>3</sup> C-H functionalization of methylhetarenes constituted crucial steps within the reaction sequences. Furthermore, gram-scale synthesis and late-stage modification of the resulting products were successfully implemented.
Authors
- Mengyuan Zhou (ORCID: https://orcid.org/0000-0003-4058-3979)
- Yuan Chen (ORCID: https://orcid.org/0000-0002-0955-1154)
- M. H. Liu
- Guodong Yin (ORCID: https://orcid.org/0000-0002-8095-0625)
- Qianqian Zhai (ORCID: https://orcid.org/0000-0002-0243-2670)
- Yifei Wang (ORCID: https://orcid.org/0000-0002-9620-4897)
- Zheng Liu (ORCID: https://orcid.org/0000-0002-0405-2348)
- Cheng Xu (ORCID: https://orcid.org/0000-0002-5350-3096)
- Tao Peng (ORCID: https://orcid.org/0009-0000-5972-9718)
Institutions
- CAS Key Laboratory of Urban Pollutant Conversion (CN)
- Hubei Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-18
- DOI
- https://doi.org/10.1021/acs.joc.5c00938
- Primary Topic
- Quinazolinone synthesis and applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Hubei Provincial Department of Education
- National Natural Science Foundation of China
- Natural Science Foundation of Hubei Province