Issue 15, 2024

Iron(ii)-catalyzed annulation to construct novel quinone-fused cyclopenta[2,1-b]indoles: a promising type I photosensitizer

Abstract

A series of novel quinone-fused cyclopenta[2,1-b]indoles was designed and conveniently constructed by an iron(II)-catalyzed annulation reaction from indolynaphthoquinones and 1,3-dicarbonyl compounds. This process involved Michael addition/radical cyclization/aromatization that achieved cyclization products with medium-to-excellent yields. These compounds exhibited near-infrared absorption and can produce O2˙. Electrochemical tests also confirmed the excellent electron-transferring ability of compound 3af, which also demonstrated excellent type I PDT effects in tumor cells.

Graphical abstract: Iron(ii)-catalyzed annulation to construct novel quinone-fused cyclopenta[2,1-b]indoles: a promising type I photosensitizer

Supplementary files

Article information

Article type
Research Article
Submitted
18 Apr 2024
Accepted
25 May 2024
First published
29 May 2024

Org. Chem. Front., 2024,11, 4119-4124

Iron(II)-catalyzed annulation to construct novel quinone-fused cyclopenta[2,1-b]indoles: a promising type I photosensitizer

H. Xu, X. Liu, B. Wang, F. Li, D. Huang, Y. Xiao, N. Ma, Y. Zhang and J. Wang, Org. Chem. Front., 2024, 11, 4119 DOI: 10.1039/D4QO00708E

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