Three-Step Synthetic Pathway toward Fully Decorated [1,2,3]Triazolo[4,5-d]pyrimidine (8-Azapurine) Derivatives
Felien Reniers1, Stijn Anthonissen1, Luc Van Meervelt2
1Sustainable Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
Abstract:
[1,2,3]Triazolo[4,5-d]pyrimidines (8-azapurines) are known bioisosteres of the purine nucleus. A step-efficient synthesis of 8-azapurines, in particular 6-alkyl derivatives, is currently unavailable. This work focuses on a three-step synthetic pathway for the synthesis of fully decorated 8-azapurines, with special attention on 6-alkyl-8-azapurines. A diverse library of 8-azapurines was obtained starting from various alkynes, azides, and amidines, involving interrupted CuAAC, oxidation, and cyclization reactions. Additionally, postfunctionalization reactions were demonstrated for a selected number of substrates.
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