一种利用恶唑酮中间体的合并羟醛缩合、烯烃异构化、环加成/环化逆转序列来合成取代吡啶的方法。
A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines.
作者信息
Williamson Jill B, Smith Emily R, Scheerer Jonathan R
机构信息
Department of Chemistry, The College of William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.
出版信息
Synlett. 2017;28(10):1170-1172. doi: 10.1055/s-0036-1588729. Epub 2017 Feb 23.
Abstract
A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.
摘要
已经评估了一种多米诺反应序列，该序列始于新型二氢恶嗪酮前体与2-炔基取代的苯甲醛组分通过羟醛缩合反应结合。随后的操作，包括烯烃异构化、狄尔斯-阿尔德反应以及伴随CO损失的逆向狄尔斯-阿尔德反应，均在同一反应容器中进行，以提供多取代的三环吡啶产物。
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3
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