Bhargava Reddy Mandapati, Prasanth Kesavan, Neerathilingam Nalladhambi, Anandhan Ramasamy
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai-600 025, India.
Org Lett. 2022 Nov 11;24(44):8158-8163. doi: 10.1021/acs.orglett.2c03222. Epub 2022 Oct 27.
Quinazolinones/benzothiadiazines were used as amidyl/aminyl radical precursors for cascade cyclizations via a photoredox-catalyzed proton-coupled electron transfer (PCET) process for the first time. A controlled synthesis of isoindole-fused quinazolinones/benzothiadiazines was carried out via quinazolinone amidyl/benzothiadiazine aminyl radical addition to the C-C triple bond under mild conditions. This transition-metal-free method provides an efficient and broad substrate scope for the synthesis of isoindole-fused quinazolinones/benzothiadiazines with step economy and atom efficiency.
喹唑啉酮/苯并噻二嗪首次被用作通过光氧化还原催化的质子耦合电子转移（PCET）过程进行级联环化的酰胺基/氨基自由基前体。在温和条件下，通过喹唑啉酮酰胺基/苯并噻二嗪氨基自由基加成到碳-碳三键上，实现了异吲哚稠合喹唑啉酮/苯并噻二嗪的可控合成。这种无过渡金属的方法为合成具有步骤经济性和原子经济性的异吲哚稠合喹唑啉酮/苯并噻二嗪提供了高效且广泛的底物范围。
