A convenient method for constructing novel tetrahydropyrido[4 ',3 ':4,5]thieno[2,3-d]-pyrimidinones-carbohydrate and amino acid conjugates via copper(I)-catalyzed alkyne-azide 'Click Chemistry'

作者：Ameen Mohamed A; Karsten Sebastian; Liebscher Juergen^*

来源：Tetrahedron, 2010, 66(12): 2141-2147.

DOI：10.1016/j.tet.2010.01.071

• Alkyne
• Azide
• Click chemistry
• Thienopyrimidinone
• Intramolecular cycloaddition

Novel conjugates of tetrahydropyridothienopyrimidones and carbohydrates of amino acids linked by 1,2,3-triazoles were synthesized After establishing the tetrahydropyridothienopyrimidones ring system by ring closure, propargyl groups were introduced by N-alkylation Cu-catalyzed cycloaddition of the propargyl products with azido group containing hexoses or amino acids gives the corresponding 1,2,3-triazoles in high yields This methodology also allowed attaching two carbohydrate molecules to the tetrahydropyridothienopyrimidone core Interesting dependence of the regioselectivity of the N-propargylation of the pyrimidone ring oil the exocyclic substituent found adjacent to the pyrimidine-N-atom was observed A remarkable case of a non-catalyzed intramolecular [3+2]-cycloaddition of an alkyne with ail azide to a 1,2,3-triazole was observed.

• 出版日期2010-3-20