DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles |
| |
Authors: | Ujjawal Kumar Bhagat Rama Krishna Peddinti |
| |
Affiliation: | Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India |
| |
Abstract: | Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4–8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. |
| |
Keywords: | Conjugate addition Cycloalkenones DABCO Organobase Triazoles |
本文献已被 ScienceDirect 等数据库收录! |
|