Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents

Abstract

We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.

Graphical Abstract

Keywords:

• 1,3-Dipolar cycloaddition
• 3(2H)-furanones
• isoxazoline
• quinoline
• nitrones

Acknowledgements

JA and SPM are thankful to CSIR for the award of Senior Research Fellowship. RN acknowledges SERB-National Post-Doctoral Fellowship for financial assistance. SAIF (STIC) CUSAT provided spectral and analytical data. Additional financial support was provided by DST-FIST, DST-PURSE and UGC-SAP. JPR is thankful to Principal, Governent Victoria College, Palakkad for providing research facilities. Authors are grateful to Professor Sreedharan Prathapan for helpful discussions.

Disclosure statement

The authors declare no conflict of interest.