Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition: efficient synthesis of 1,2,3-triazolo beta-hydroxy or beta-tosylamino functionality motif.
A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.
Kumaraswamy
Gullapalli
G
Organic Division III, Fine Chemicals Laboratory, Indian Institute of Chemical Technology, Hyderabad-500 007, India. gkswamy_iict@yahoo.co.in
Ankamma
Kukkadapu
K
Pitchaiah
Arigala
A
D001386:Azides / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D001388:Aziridines; D004852:Epoxy Compounds; D014105:Tosyl Compounds; D014230:Triazoles; D003300:Copper