Tetrahedron

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

HJ Kim, DK Dogutan, M Ptaszek, JS Lindsey

Index: Kim, Han-Je; Dogutan, Dilek Kiper; Ptaszek, Marcin; Lindsey, Jonathan S. Tetrahedron, 2007 , vol. 63, # 1 p. 37 - 55

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Citation Number: 20

Abstract

A collection of 33 hydrodipyrrins (9 targets, 21 intermediates, and 3 byproducts) has been prepared. The hydrodipyrrins (dihydrodipyrrins, tetrahydrodipyrrins, and hexahydrodipyrrins) contain a pyrrole ring and a geminal-dimethyl substituted 1-pyrroline (or pyrrolidine) ring. The α-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 ...