ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Regioselective reactions of methyl pyropheophorbide a with formaldehyde based on hydroxymethylation

Yang Liu, Huiqiang Wu, Xiao Zhang, Qiang Pan, Xiangmin Wang, Wei Peng, Jungang Yin, Guizhi Li, Jiazhu Li, and Jinjun Wang

Yantai University, Yantai, China

E-mail: lgz2001@126.com

Abstract: Regioselective reactions of methyl pyropheophorbide a (MPPa) with formaldehyde based on hydroxymethylation have been studied. It was found that MPPa can react regioselectively with formaldehyde under different conditions to produce a series of 3-dioxane, 12-, 13²- or 20-hydroxymethyl and 12-/13²-alkenyl-substituted chlorins via Prins reaction, Blanc chloromethylation and aldol reaction, respectively. The first examples of direct C–C bond formation at 12-position of chlorophyll derivatives were also reported to give a series of 12-vinyl-substituted chlorins. These chlorins showed extend Qy absorptions and efficient singlet oxygen generation property, indicating their potential as photosensitizers for application in photodynamic therapy.

Keywords: Chlorophyll a ; Chlorin ; Prins reaction ; Blanc chloromethylation ; Aldol reaction 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0376-4

Chemical Papers 72 (6) 1389–1398 (2018)