Unusual Cu(I)-catalyzed 1,3-dipolar cycloaddition of acetylenic amides: formation of bistriazoles

C-carbamoyl-1,2,3-triazoles have recently attracted much interest due to their potent biological activity. While synthesizing C-carbamoyl-1,2,3-triazoles by the copper(I)-catalyzed 1,3-dipolar cycloaddition of organic azides 1 and acetylenic amides 2, we found that the expected 1,2,3-triazole produc...

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Bibliographic Details
Published in:Tetrahedron letters 2012-03, Vol.53 (13), p.1606-1609
Main Authors: Kwon, Mihyun, Jang, Yujin, Yoon, Sunyoung, Yang, Dongsik, Jeon, Heung Bae
Format: Article
Language:English
Subjects:
Acetylenic amide
Amides
Biological
Bistriazole
C-carbamoyl-1,2,3-triazole
Cu(I)-catalyzed 1,3-dipolar cycloaddition
Cycloaddition
Formations
Sodium
Tetrahedrons
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Summary:C-carbamoyl-1,2,3-triazoles have recently attracted much interest due to their potent biological activity. While synthesizing C-carbamoyl-1,2,3-triazoles by the copper(I)-catalyzed 1,3-dipolar cycloaddition of organic azides 1 and acetylenic amides 2, we found that the expected 1,2,3-triazole products 3 were obtained as the only products in excellent yields when CuSO4 and sodium ascorbate were used as the Cu(I)-catalyst. Surprisingly, the unexpected bistriazole products 4 were one of the major products obtained along with the 1,2,3-triazoles 3 when using a direct Cu(I)-catalyst such as CuI or CuBr.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.01.069