A facile synthesis of cyano-chlorins related to chlorophyll from formyl (pyro)-pheophorbide-a by a tandem transformation of the aldehyde into a nitrile group

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• 作者：Na Gao^a ; Jia-Zhu Li^b ; ^{lijiazhu@163.com" class="auth_mail" title="E-mail the corresponding author} ; Yan-Long Li^b ; Zhen Wang^b ; Jin-Jun Wang^a ; ^b ; ^{wjj1955@163.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Chlorophyll-a ; Chlorin ; (Pyro)pheophorbide-a ; Cyanation reaction ; Beckmann rearrangement ; Tandem transformation
• 刊名：Chinese Chemical Letters
• 出版年：2016
• 出版时间：May 2016
• 年：2016
• 卷：27
• 期：5
• 页码：789-794
• 全文大小：826 K

文摘

A facile synthesis for cyanochlorin related to chlorophyll from a formyl-substituted chlorin, by the oxidation of methyl (pyro)pheophorbide-a, was accomplished. These readily available chlorin aldehydes were assembled together with hydroxylamine hydrochloride in a tandem process to produce the corresponding chlorin nitriles in moderate to good yields. The formation of chlorin nitrile was discussed and a possible mechanism for the corresponding cyanation reaction was tentatively proposed.