Tetrahedron

Competing Knorr and Fischer–Fink pathways to pyrroles in neutral aqueous solution

V Chandrashaker, M Taniguchi, M Ptaszek, JS Lindsey

Index: Chandrashaker, Vanampally; Taniguchi, Masahiko; Ptaszek, Marcin; Lindsey, Jonathan S. Tetrahedron, 2012 , vol. 68, # 34 p. 6957 - 6967

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Citation Number: 15

Abstract

A proposed chemical model for the prebiogenesis of tetrapyrrole macrocycles relies on the condensation of a 3-alkyl-substituted 2, 4-diketone and an α-aminoketone to form a pyrrole equipped for subsequent self-condensation leading to porphyrinogens. The condensation of acyclic reactants can proceed via competing Knorr (desired) and Fischer–Fink (undesired) pathways. Here, the Knorr and Fischer–Fink pathways are quantitated using (1) ...

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