Functionalized cyclic nitrones:
Multicomponent synthetic approach
and reactivity study
Marian Buchlovič
Department of Chemistry, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
New type of multicomponent reaction leading to 5-membered functionalized cyclic nitrones will be
presented. Reaction design is based upon unique reactivity of allenyloxime in the presence of different
primary alcohols and aldehydes (see scheme). Optimization of reaction conditions and evaluation of
reaction scope was followed by a study of reactivity. 1,3-Dipolar cycloadditions in the presence of
various dipolarophiles were tested. In addition, unique chemistry of selected derivatives was found and
studied in detail. Nitrones that contained planar aromatic polycycles in their structure showed ability to
interact with DNA helix. Theoretical and experimental studies related to biological activity will be
discussed.
•
N
OH
R2
HO
R1
O
N O
R2
O
R1
H
+
tBuOK
tBuOH, 80°C
References:
• Buchlovič M., Man S., Potáček M.: Synthesis 2012, 44, 973.
• Buchlovič M., Man S., Kislitson K., Mathot S., Potáček M.: Tetrahedron 2010, 66, 1821.
• Buchlovič M., Man S., Potáček M.: Tetrahedron 2008, 64, 9953.
• Buchlovič M., Man S., Potáček M.: Tetrahedron Lett. 2010, 51, 5801.
• Buchlovič M., Hebanová S., Potáček M.: Tetrahedron 2012, 68, 3117.