Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridin intermediates.
[reaction: see text] A short synthesis of the C(11)N(5) oroidin derivatives is reported. The key step of the strategy is a one-pot oxidative bromine-mediated addition of protected guanidines to the N-acyl-1,2-dihydropyridines 9a-c. The new N-acyl-1,2-dihydropyridines were prepared directly from pyridine and pyrrole-2-carbonyl chloride by reduction with borohydride reagent in one step.
Schroif-Gregoire
Cosima
C
Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France.
Travert
Nathalie
N
Zaparucha
Anne
A
Al-Mourabit
Ali
A
D002384:Catalysis; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008386:Marine Biology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D007093:Imidazoles; D007202:Indicators and Reagents; D011725:Pyridines; D011758:Pyrroles; C077209:oroidin