Reaction of Quinones and Guanidine Derivatives: Simple Access to Bis-2-aminobenzimidazole Moiety of Benzosceptrin and Other Benzazole Motifs

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• 作者：Minh Quan Tran ; Ludmila Ermolenko ; Pascal Retailleau ; Thanh Binh Nguyen ; Ali Al-Mourabit
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：16
• 期：3
• 页码：920-923
• 全文大小：315K
• ISSN：1523-7052

文摘

A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1鈥?2鈥?4,5]imidazo[1,2-a]pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.