Issue 10, 2018

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Jan 2018
Accepted
08 Feb 2018
First published
08 Feb 2018

Org. Biomol. Chem., 2018,16, 1686-1691

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

G. A. M. Jardim, W. X. C. Oliveira, R. P. de Freitas, R. F. S. Menna-Barreto, T. L. Silva, M. O. F. Goulart and E. N. da Silva Júnior, Org. Biomol. Chem., 2018, 16, 1686 DOI: 10.1039/C8OB00196K

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