Peer-Reviewed Journal Details
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Eamonn Joyce, Padraig McArdle, Fawaz Aldabbagh
2011
May
Synlett
Acetic Anhydride Generated Imidazolium Ylide in Ring Closures onto Carboxylic Acids; Part of the Synthesis of New Potential Bioreductive Antitumor Agents
Published
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Optional Fields
benzimidazoles condensation heterocycles quinones ylides 5-MEMBERED N-HETEROCYCLES 2-SUBSTITUTED AZOLES ACYLATION REACTIONS C-ACYLATION WATER
1097
1100
Acetic anhydride behaves as a traceless activating agent allowing thermal intramolecular condensation of 2-(benzimidazol-1-ylmethyl) benzoic and nicotinic acids. Autoxidation gives benzimidazo[1,2-b]isoquinoline-6,11-diones (intermediates characterized) and benzimidazo[2,1-g]-1,7-naphthyridine-5,12-diones in a facile, one-pot transformation. The 1,4-dimethoxy analogue of the former is converted into benzimidazo[1,2-b]isoquinoline-1,4,6,11-tetrone using cerium ammonium nitrate (CAN). The 1,7-naphthyridine-5,12-dione system readily ring-opens, and an X-ray crystal structure of the methanol adduct was obtained.
https://www.thieme-connect.com/ejournals/abstract/10.1055/s-0030-1260543
DOI 10.1055/s-0030-1260543
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