title: Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids: Ab initio calculations, tautomerism, and reactivity.
abstract: [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.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
authors.forename: Robert
authors.initials: R
authors.lastname: Abou-Jneid
authors.forename: Said
authors.initials: S
authors.lastname: Ghoulami
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.forename: Elise Tran Huu
authors.initials: ET
authors.lastname: Dau
authors.forename: Nathalie
authors.initials: N
authors.lastname: Travert
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit