Peer-Reviewed Journal Details
Mandatory Fields
Hehir, S,O'Donovan, L,Carty, MP,Aldabbagh, F
2008
May
Tetrahedron
Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones
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Optional Fields
antitumor agents azifidinylimines cycloaddition heterocycles BIOREDUCTIVE ANTICANCER AGENTS MODIFIED ANTITUMOUR AGENTS CYCLOPROPAMITOSENES CYCLOADDITION
64
4196
4203
Upon thermolysis 5.6-dimethyl-N- [(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-l-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells. (c) 2008 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tet.2008.02.093
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