"One-pot" access to dihydrofurans via tandem oxidative difunctionalization and ring contraction of aminopyrans.
An operationally simple and efficient protocol for the construction of dihydrofuran derivatives has been accomplished via a sequential addition of N-chlorosuccinimide and a base to 2-amino-4H-pyran derivatives in alcohol medium. The one-pot protocol proceeding via tandem oxidative difunctionalization and ring contraction provides an entirely new strategy for the construction of the dihydrofuran skeleton.
Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, India. manjula@iict.res.in.
Santhosh Reddy
SR
Mandha
Manjula
M
Alla
Jagadeesh Babu
JB
Nanubolu
D002625:Chemistry, Organic / Q000379:methods*; D004951:Esterification; D004952:Esters / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006868:Hydrolysis; D006878:Hydroxides / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D017680:Potassium Compounds / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000737:chemistry*
D004952:Esters; D005663:Furans; D006878:Hydroxides; D017680:Potassium Compounds; D011714:Pyrans; C029943:potassium hydroxide; D000432:Methanol