Gryko Daniel T, Gałezowski Michał
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
Org Lett. 2005 Apr 28;7(9):1749-52. doi: 10.1021/ol050327a.
[reaction: see text] A novel synthetic approach to diversely functionalized "locked" chlorins is described. A suitably substituted 2,5-diformylpyrrole undergoes the macrocyclization reaction with tripyrranes, thereby generating porphyrins. Upon the reaction with 1,3-dipoles these porphyrins regioselectively furnish pyrrolidine-fused chlorins, which cannot oxidize to the corresponding porphyrins. In the process involving just six steps from commercially available and cheap materials we are able to obtain approximately 200 mg of pure stable chlorins (the overall yield is 1.5-2.8%).
[反应：见正文] 描述了一种合成多种官能化“锁定”二氢卟吩的新方法。适当取代的2,5-二醛基吡咯与三吡咯发生大环化反应，从而生成卟啉。这些卟啉与1,3-偶极体反应时，区域选择性地生成吡咯烷稠合的二氢卟吩，其不能氧化为相应的卟啉。在从市售廉价材料开始仅涉及六个步骤的过程中，我们能够获得约200 mg的纯稳定二氢卟吩（总产率为1.5 - 2.8%）。
