Solid-supported nitroso hetero diels-alder reactions. 2. Arylnitroso dienophiles: scope and limitations.
Immobilized arylnitroso dienophiles were prepared and used in hetero Diels-Alder (HDA) reactions with a variety of dienes. Polymer-supported arylnitroso species were prepared on several linkers cleavable by different cleavage reagents and used for (i) optimization of reaction conditions for HDA reactions, (ii) evaluation of the reaction outcome with various dienes, (iii) comparison of relative reactivities of dienes, and (iv) assessment of the stability of HDA adducts toward cleavage conditions typically used in solid-phase preparation (TFA). The outcome of the HDA reactions has been evaluated for a set of 19 dienes, and the relative reactivities of dienes that yielded the expected HDA adducts were compared. Cleaved products were submitted to biological assays, and the results are reported.
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA. vkrchnak@nd.edu
Viktor
V
Krchnák
Ute
U
Moellmann
Hans-Martin
HM
Dahse
Marvin J
MJ
Miller
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D005240:Feasibility Studies; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*
D006571:Heterocyclic Compounds; D009603:Nitroso Compounds; D011108:Polymers