AI Article Synopsis

  • A new method is introduced for creating 2-aminobenzimidazol-6-ols through the reaction of quinones with guanidine derivatives.
  • This approach enabled the successful synthesis of the first benzosceptrin analogue featuring a bis-2-aminoimidazole structure.
  • The process involved adding two guanidines to a specific compound, allowing for simultaneous redox neutral debezylation and cleavage, resulting in the complex bis-2-aminoimidazole moiety of benzosceprins being formed in one step.

Article Abstract

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',2':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.

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http://dx.doi.org/10.1021/ol403672pDOI Listing

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