Heterocyclization of functionalized vinylic derivatives of imidazo.
Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-a]pyridines was explored experimentally and theoretically using semiempirical AM1 and ab initio methods. A range of functionalized vinylic derivatives (azido, amino, and carbodiimide groups) were prepared for conversion into pyrroloazaindoles 19-22, imidazo[1,x]-, (x = 5, 6, 7, 8), [2,6]-, and [2,7]naphthyridines 28-30, 35-38 by thermal reaction. In the case of vinylic groups in the 5 position, peri annulation also was observed. The experimental and theoretical data are compared and discussed.
Chezal
J M
JM
UMR INSERM 484, Université d'Auvergne, Faculté de Pharmacie, 28 Pl. H. Dunant, B.P. 38, 63001 Clermont-Ferrand CEDEX 1, France.
Moreau
E
E
Delmas
G
G
Gueiffier
A
A
Blache
Y
Y
Grassy
G
G
Lartigue
C
C
Chavignon
O
O
Teulade
J C
JC
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006801:Humans; D008958:Models, Molecular; D019636:Neurodegenerative Diseases / Q000188:drug therapy; D011725:Pyridines / Q000138:chemical synthesis*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D006571:Heterocyclic Compounds; D011725:Pyridines; C001439:imidazo(1,2-a)pyridine