Krchnák Viktor, Moellmann Ute, Dahse Hans-Martin, Miller Marvin J
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA.
J Comb Chem. 2008 Jan-Feb;10(1):104-11. doi: 10.1021/cc7001414. Epub 2007 Dec 7.
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.
制备了固定化芳基亚硝基亲双烯体，并将其用于与多种双烯的杂环狄尔斯-阿尔德（HDA）反应。在几种可被不同裂解试剂裂解的连接基上制备了聚合物负载的芳基亚硝基物种，并将其用于：（i）优化HDA反应的条件；（ii）评估与各种双烯反应的结果；（iii）比较双烯的相对反应活性；（iv）评估HDA加合物对通常用于固相制备的裂解条件（三氟乙酸）的稳定性。对一组19种双烯的HDA反应结果进行了评估，并比较了生成预期HDA加合物的双烯的相对反应活性。将裂解产物进行生物学测定，并报告结果。
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