4‐Phosphonated or 4‐Free 1,2,3‐Triazoles: What Controls the Dimroth Reaction of Arylazides with 2‐Oxopropylphosphonates?

The influence of base‐solvent systems and substituents on the reaction of aryl azides with dimethyl 2‐oxopropylphosphonate was studied. It was shown that azides with electron‐withdrawing substituents in K2CO3/DMSO medium (mild conditions) afford 5‐methyl‐1‐aryl‐1H‐1,2,3‐triazole‐4‐ylphosphonates as...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2020-01, Vol.5 (1), p.260-264
Main Authors: Pokhodylo, Nazariy T., Shyyka, Olga Ya, Goreshnik, Evgeny A., Obushak, Mykola D.
Format: Article
Language:English
Subjects:
1,2,3-Triazoles
Azide
Cycloaddition
Selectivity
β-Ketophosphonates
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Summary:The influence of base‐solvent systems and substituents on the reaction of aryl azides with dimethyl 2‐oxopropylphosphonate was studied. It was shown that azides with electron‐withdrawing substituents in K2CO3/DMSO medium (mild conditions) afford 5‐methyl‐1‐aryl‐1H‐1,2,3‐triazole‐4‐ylphosphonates as major products. In contrast, azides with electron‐donating substituents produce 1‐aryl‐5‐methyl‐1H‐1,2,3‐triazoles. Based on the obtained results the plausible mechanisms of the reactions were discussed and key points of selectivity control were indicated. The reaction of aryl azides with dimethyl 2‐oxopropylphosphonate was studied. The 5‐methyl‐1‐aryl‐1H‐1,2,3‐triazole‐4‐ylphosphonates were major products when azides with electron‐withdrawing substituents in K2CO3/DMSO medium (mild conditions) were used. The plausible mechanisms of the reactions were discussed and key points of selectivity control were indicated.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201904688