Acetic Anhydride Generated Imidazolium Ylide in Ring Closures onto Carboxylic Acids; Part of the Synthesis of New Potential Bioreductive Antitumor Agents

Abstract 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-naphthyrid...

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Bibliographic Details
Published in:Synlett 2011-05, Vol.2011 (8), p.1097-1100
Main Authors: Joyce, Eamonn, McArdle, Patrick, Aldabbagh, Fawaz
Format: Article
Language:English
Subjects:
Antineoplastic agents
Biological and medical sciences
Chemistry
Exact sciences and technology
General aspects
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
letter
Medical sciences
Noncondensed benzenic compounds
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
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Summary:Abstract 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1260543