Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids: Ab initio calculations, tautomerism, and reactivity.
[reaction: see text] A simple synthesis of the fused tetrahydro-imidazopyridine 13 was accomplished via selective addition of protected guanidine to N-carbomethoxy-1,2-dihydropyridine in the presence of bromine. Base-mediated semicleavage of the aminal gave 4-substituted 2-aminoimidazole 14. With this new method, natural marine metabolite 3-amino-1-(2-aminoimidazol-4-yl)-prop-1-ene (1) and derivatives may now be prepared from pyridine. Ab initio calculations of the energies of tautomers I-IV and deuteration experiments have provided insight into their reactivity.
Abou-Jneid
Robert
R
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Ghoulami
Said
S
Martin
Marie-Thérèse
MT
Dau
Elise Tran Huu
ET
Travert
Nathalie
N
Al-Mourabit
Ali
A