5-BROMO-3-CHROMANECARBOXYLIC ACID

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CAS: 701-37-1
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Synonyms: 5-BROMO-3-CHROMANECARBOXYLIC ACID

REPORT BY

Christopher Hulme

The University of Arizona
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Co-reporter: Muhammad Ayaz, Zhigang Xu, Christopher Hulme
pp: 3406-3409
Publication Date(Web):4 June 2014
DOI: 10.1016/j.tetlet.2014.04.013
This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a ‘convertible carboxylic acid’, which in addition may be captured in an intramolecular sense to generate structurally complex 2-benzimidazolylquinoxalines in a mere two steps.Image for unlabelled figure