title: Intramolecular Diels-Alder chemistry of 4-vinylimidazoles.
abstract: An investigation of 4-vinylimidazoles as diene components in the intramolecular Diels-Alder reaction is described. In the course of these studies several parameters affecting the cycloaddition were evaluated including the nature of the imidazole protecting group, the type of dienophile and the linking group. These investigations established that amino linkers were generally more effective than either ethers or esters. In most cases, the cycloadditions were highly stereoselective, resulting in the formation of products derived from an anti transition state. The polysubstituted tetrahydrobenzimidazole core of the pyrrole-imidazole alkaloid ageliferin can be constructed through the use of pseudo dimeric 4-vinylimidazoles.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas, USA.
authors.forename: Yong
authors.initials: Y
authors.lastname: He
authors.forename: Pasupathy
authors.initials: P
authors.lastname: Krishnamoorthy
authors.forename: Heather M
authors.initials: HM
authors.lastname: Lima
authors.forename: Yingzhong
authors.initials: Y
authors.lastname: Chen
authors.forename: Haiyan
authors.initials: H
authors.lastname: Wu
authors.forename: Rasapalli
authors.initials: R
authors.lastname: Sivappa
authors.forename: H V Rasika
authors.initials: HV
authors.lastname: Dias
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Lovely
mesh_terms: D003500:Cyclization; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D014753:Vinyl Compounds