Bousfiha Asmae, Amiri Nesrine, Akhssas Fatima, Berthelot Mathieu, Echaubard Julie, Pirrotta Marc, Cattey Hélène, Fleurat-Lessard Paul, Roger Julien, Devillers Charles H
Institut de Chimie Moléculaire de l'Université de Bourgogne UMR6302, CNRS, Univ. Bourgogne, 9 avenue Alain Savary, 21000 Dijon, France.
Org Lett. 2023 Nov 10;25(44):7979-7983. doi: 10.1021/acs.orglett.3c03062. Epub 2023 Nov 1.
5,15-Bis(pyrimidin-2-ylthio)porphyrins have been synthesized. Their electrochemical oxidation leads to the formation of mono- and bis-C-N-fused thiopyrimidinium intermediates depending on the applied charge and potential. These latter undergo nucleophilic attack with water during workup that drives the ring opening of the pyrimidinium moiety. When piperidine is added before or after workup, the neutral fused porphyrinthiazin-2-amines are generated, and they exhibit a significant bathochromic shift of their Soret and Q bands.
已合成了5,15-双（嘧啶-2-基硫代）卟啉。根据施加的电荷和电势，它们的电化学氧化会导致形成单-C-N-稠合和双-C-N-稠合的硫代嘧啶鎓中间体。在后处理过程中，这些中间体与水发生亲核进攻，从而促使嘧啶鎓部分开环。当在后处理之前或之后加入哌啶时，会生成中性的稠合卟啉噻嗪-2-胺，并且它们的Soret带和Q带出现明显的红移。
