Direct sequential C-H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: a new protocol for potent trypanocidal quinones

We report a sequential C-H iodination/organoyl-thiolation of naphthoquinones and their relevant trypanocidal activity. Under a combination of AgSR with a copper source, sulfur-substituted benzenoid quinones were prepared in high yields (generally >90%). This provides an efficient and general meth...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018, Vol.16 (10), p.1686-1691
Main Authors: Jardim, Guilherme A M, Oliveira, Willian X C, de Freitas, Rossimiriam P, Menna-Barreto, Rubem F S, Silva, Thaissa L, Goulart, Marilia O F, da Silva Júnior, Eufrânio N
Format: Article
Language:English
Subjects:
Deactivation
Iodination
Quinones
Sulfur
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Summary:We report a sequential C-H iodination/organoyl-thiolation of naphthoquinones and their relevant trypanocidal activity. Under a combination of AgSR with a copper source, sulfur-substituted benzenoid quinones were prepared in high yields (generally >90%). This provides an efficient and general method for preparing A-ring modified naphthoquinoidal systems, recognized as a challenge in quinone chemistry.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00196k