Synthesis of hydrodipyrrins tailored for reactivity at the 1- and 9-positions

TETRAHEDRON

卷:63

Article

Kim, Han-Je ; Dogutan, Dilek Kiper ; Ptaszek, Marcin ; Lindsey, Jonathan S.

关键词: hydrodipyrrin;    1-pyrroline;    pyrrole;    hydroporphyrin;   

DOI  :  10.1016/j.tet.2006.10.027

来源: Elsevier

【 摘 要 】

A collection of 33 hydrodipyrrins (9 targets, 21 intermediates, and 3 byproducts) has been prepared. The hydrodipyrrins (dihydrodipyrrins, tetrahydrodipynins, and hexahydrodipyrrins) contain a pyrrole ring and a gerninal-dimethyl substituted 1-pyrroline (or pyrrolidine) ring. The alpha-substituents on the pyrrole ring (H, Br, CHO) and pyrroline ring (H, CH3, CH(OR)(2), OMe, SMe) provide different reactivity combinations (Nu(-), E+) and 0, 1, or 2 carbon atoms (which can give rise to the bridging meso-carbons in hydroporphyrins). Straightforward access to various hydrodipyrrins should facilitate development of syntheses of diverse hydroporphyrins. (c) 2006 Elsevier Ltd. All rights reserved.

【 授权许可】

Free