Efficient method for the synthesis of 1,2,3-triazole functionalized isoxazolidine derivatives by 1,3-dipolar cycloaddition of nitrones with terminal olefins

ABSTRACT

1-Phenyl-1,2,3-triazole-4-carbaldehyde 1 was treated with different N-alkyl hydroxylamine hydrochlorides 2 using NaHCO₃ to obtain 1,2,3-triazole substituted N-alkyl nitrones 3a–c. The nitrones 3a–c were further reacted with different substituted olefins and furnished 2-alkyl-3-(1-phenyl-1H-1,2,3-triazol-4-yl)-5-(substituted)isoxazolidine derivatives 4a–p in high yields via 1,3-dipolar cycloaddition reaction.

GRAPHICAL ABSTRACT

KEYWORDS:

• 1,3-Dipolar cycloaddition
• isoxazolidine
• nitrones
• olefins
• 1,2,3-triazole

Acknowledgments

B. Narsaiah, K. Chinna Ashalu, P.V.S.S. Srinivas, and B.V. Thomas are thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India for providing funding through XII five year plan project DITSF code: CSC-0204. The other authors are also thankful to the CSIR, New Delhi, India for providing financial assistance in the form of senior research fellowships.