Iodine-promoted amide formation via oxidative cleavage of indoles: novel quinazoline-4(3 H )-one and tryptanthrin syntheses.
| Autor: | Le PQ; School of Biotechnology, International University-VNU HCM Quarter 6, Linh Trung Ward, Thu Duc City Ho Chi Minh City Vietnam lqphong@hcmiu.edu.vn.; Vietnam National University Ho Chi Minh City Linh Trung Ward, Thu Duc City Ho Chi Minh City Vietnam., Dinh VM; Department of Chemistry, Chemical-Biological Centre, Umeå University SE-90187 Umeå Sweden., Nguyen HDT; Faculty of Chemistry, University of Science 227 Nguyen Van Cu, District 5 Ho Chi Minh City Vietnam.; Vietnam National University Ho Chi Minh City Linh Trung Ward, Thu Duc City Ho Chi Minh City Vietnam., Ha HQ; Institute of Applied Technology and Sustainable Development, Nguyen Tat Thanh University Ho Chi Minh City 755414 Vietnam hiepquangha@gmail.com., Truong TV; Faculty of Chemical Engineering, Ho Chi Minh City University of Technology 268 Ly Thuong Kiet, District 10 Ho Chi Minh City Vietnam truongvuthanh@gmail.com.; Vietnam National University Ho Chi Minh City Linh Trung Ward, Thu Duc City Ho Chi Minh City Vietnam. |
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| Jazyk: | angličtina |
| Zdroj: | RSC advances [RSC Adv] 2024 May 14; Vol. 14 (22), pp. 15597-15603. Date of Electronic Publication: 2024 May 14 (Print Publication: 2024). |
| DOI: | 10.1039/d4ra01807a |
| Abstrakt: | A highly efficient method for the direct construction of amide bonds via a selective cleavage of C-H and C[double bond, length as m-dash]C bonds in indole structures using an iodine-promoted approach was developed. Mechanistic studies indicated the formation of superoxide radicals obtained from molecular oxygen activation as a key intermediate step, which provided a precursor for subsequent oxidative ring-opening and intermolecular cyclization. A broad range of quinazolin-4(3 H )-ones and tryptanthrins were synthesized in moderate to good yields under mild and environmentally benign conditions. Competing Interests: There are no conflicts of interest to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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