Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids: Ab initio calculations, tautomerism, and reactivity

Autor: Said Ghoulami, Ali Al-Mourabit, Marie-Thérèse Martin, Elise Tran Huu Dau, Nathalie Travert, Robert Abou-Jneid
Rok vydání: 2004
Předmět:
Zdroj: Organic letters. 6(22)
ISSN: 1523-7060
Popis: [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.
Databáze: OpenAIRE