Electrochemically enabled synthesis of sulfide imidazopyridinesviaa radical cyclization cascade
Owing to the inert nature of the pyridine ring and high activity of iminyl radicals, the reaction between pyridine and iminyl radicals remains a significant challenge. In this paper, we report the synthesis of sulfide imidazo[1,2-a]pyridines from vinyl azides, thiophenols, and pyridinesviaa radical...
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| Published in | Green chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 19; pp. 6334 - 6339 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | Owing to the inert nature of the pyridine ring and high activity of iminyl radicals, the reaction between pyridine and iminyl radicals remains a significant challenge. In this paper, we report the synthesis of sulfide imidazo[1,2-a]pyridines from vinyl azides, thiophenols, and pyridinesviaa radical [3 + 2] cycloaddition. Promoting inert pyridine and highly active iminyl radicals to participate in this intermolecular cycloaddition process is the striking feature of this protocol. The excellent antitumor activity of the prepared sulfide imidazopyridine scaffold demonstrated the synthetic utility of the developed synthetic protocol. |
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| AbstractList | Owing to the inert nature of the pyridine ring and high activity of iminyl radicals, the reaction between pyridine and iminyl radicals remains a significant challenge. In this paper, we report the synthesis of sulfide imidazo[1,2-a]pyridines from vinyl azides, thiophenols, and pyridinesviaa radical [3 + 2] cycloaddition. Promoting inert pyridine and highly active iminyl radicals to participate in this intermolecular cycloaddition process is the striking feature of this protocol. The excellent antitumor activity of the prepared sulfide imidazopyridine scaffold demonstrated the synthetic utility of the developed synthetic protocol. |
| Author | Tang, Hai-Tao Meng, Xiu-Jin Wang, Lin-Wei Pan, Ying-Ming Mo, Zu-Yu Lin, Hong-Min Zhong, Ping-Fu |
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| Cites_doi | 10.1021/jm800203e 10.1002/anie.201605548 10.1039/c9gc01098j 10.1002/anie.201710618 10.1021/acs.accounts.9b00472 10.1021/ar500017f 10.1021/cr200251d 10.1039/c5cs00852b 10.1021/acs.orglett.7b03204 10.1021/acs.chemrev.7b00475 10.1002/anie.201101009 10.1021/acs.orglett.9b02616 10.1021/acscatal.9b02830 10.1021/acs.chemrev.7b00271 10.1039/c6gc00666c 10.1126/science.aat4133 10.1021/acs.accounts.9b00512 10.1002/anie.201610715 10.1038/s41467-019-08413-9 10.1021/acs.chemrev.7b00763 10.1021/jm050610f 10.1021/acs.orglett.7b01771 10.1002/anie.201705122 10.1021/acs.chemrev.8b00233 10.1021/jacs.7b03262 10.1021/jm049484q 10.1002/anie.201706270 10.1002/adsc.201901115 10.1002/anie.201307846 10.1021/acscatal.9b03798 10.1039/c7cs00017k 10.1021/ja905110c 10.1021/ja402833w |
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| Keywords | DESIGN VINYL AZIDES PYRIDINE TRIFLUOROMETHYLATION |
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| Title | Electrochemically enabled synthesis of sulfide imidazopyridinesviaa radical cyclization cascade |
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