Regioselective anionic [3+2] cyclizations of imidazole dinucleophiles withoxaldiimidoyl dichlorides - A combined experimental and theoretical study

Citation
P. Langer et al., Regioselective anionic [3+2] cyclizations of imidazole dinucleophiles withoxaldiimidoyl dichlorides - A combined experimental and theoretical study, EUR J ORG C, (12), 2001, pp. 2245-2255
Citations number
67
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434-193X → ACNP
Issue
12
Year of publication
2001
Pages
2245 - 2255
Database
ISI
SICI code
1434-193X(200106):12<2245:RA[COI>2.0.ZU;2-E
Abstract
Regioselective cyclization reactions between oxaldiimidoyl dichlorides and imidazole-derived dinucleophiles provide convenient access to biologically relevant diazabicyclo[2.2.1]heptanones, 1H-pyrrolo[ 1,2-alpha ]benzimidazol es, 3H-imidazo[1,2-alpha ]benzimidazoles and 2,3-dihydrothiazolo[3,2,alpha ]benzimidazoles. All cyclizations proceed with good regioselectivity, direc ted by the heteroatoms of the dinucleophile. The tautomeric forms of the st ructurally mobile benzimidazoles have been studied both in solution and in the solid state. The structural properties and the regioselectivities are e xplained by semiempirical calculations.