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Regioselective Anionic [3+2] Cyclizations of Imidazole Dinucleophiles with Oxaldiimidoyl Dichlorides − A Combined Experimental and Theoretical Study
Author(s) -
Langer Peter,
Wuckelt Jörg,
Döring Manfred,
Schreiner Peter R.,
Görls Helmar
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200106)2001:12<2245::aid-ejoc2245>3.0.co;2-c
Subject(s) - chemistry , regioselectivity , imidazole , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis
Regioselective cyclization reactions between oxaldiimidoyl dichlorides and imidazole‐derived dinucleophiles provide convenient access to biologically relevant diazabicyclo[2.2.1]heptanones, 1 H ‐pyrrolo[1,2‐ a ]benzimidazoles, 3 H ‐imidazo[1,2‐ a ]benzimidazoles and 2,3‐dihydrothiazolo[3,2‐ a ]benzimidazoles. All cyclizations proceed with good regioselectivity, directed by the heteroatoms of the dinucleophile. The tautomeric forms of the structurally mobile benzimidazoles have been studied both in solution and in the solid state. The structural properties and the regioselectivities are explained by semiempirical calculations.