TFE-Facilitated Synthesis of Tetrahydropyridino[2,3- d]pyrimidine via Cascade [1,5]-Hydride Transfer/Cyclization

Cong Wei; Yan Li; Xin Yao; Kui Zhang; Lingchao Cai

doi:10.1021/acs.joc.3c02004

TFE-Facilitated Synthesis of Tetrahydropyridino[2,3- d]pyrimidine via Cascade [1,5]-Hydride Transfer/Cyclization

J Org Chem. 2023 Dec 15;88(24):17144-17154. doi: 10.1021/acs.joc.3c02004. Epub 2023 Nov 27.

Authors

Cong Wei¹, Yan Li¹, Xin Yao¹, Kui Zhang¹, Lingchao Cai¹

Affiliation

¹ Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Jiangsu Province Key Laboratory of Green Biomass-Based Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

PMID: 38010354
DOI: 10.1021/acs.joc.3c02004

Abstract

An efficient fluorinated alcohol-driven cascade [1,5]-hydride transfer/cyclization between o-amino pyridyl aldehydes and primary amines has been developed. This unique transformation enabled an array of tetrahydropyridino[2,3-d]pyrimidine construction. Furthermore, the encouraging antifungal activity of Thanatephorus cucumeris was demonstrated by this tetrahydropyridino[2,3-d]pyrimidine core structure.