Dipolar cycloaddition of novel 6-(nitrileoxidomethyl) penam sulfone: an efficient route to a new class of beta-lactamase inhibitors.
6-(Nitrileoxidomethyl) penam sulfone intermediate was prepared in a few steps starting from commercially available (+)-6-aminopenicillanic acid. This intermediate underwent smooth 1, 3-dipolar cycloaddition reactions with various alkenes and alkynes to give cycloadducts in moderate to good yields. By this new method, several potent beta-lactamase inhibitors were synthesized. The regio- and stereoselectivity outcomes of the cycloaddition process are also discussed.
Sandanayaka
V P
VP
Chemical Sciences and Infectious Diseases, Wyeth-Ayerst Research, 401 North Middletown Road, Pearl River, New York 10965, USA. sandanv@war.wyeth.com
Yang
Y
Y
D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007555:Isoxazoles / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry; D065093:beta-Lactamase Inhibitors
C415672:6-(nitrileoxidomethyl) penam sulfone; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D007555:Isoxazoles; D009570:Nitriles; D013450:Sulfones; D065093:beta-Lactamase Inhibitors