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Synthesis 2001; 2001(4): 0541-0543
DOI: 10.1055/s-2001-12346
short paper
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Hypervalent Iodine Oxidative Rearrangement of Anthranilamides, Salicylamides and Some β-Substituted Amides: A New and Convenient Synthesis of 2-Benzimidazolones, 2-Benzoxazolones and Related Compounds

Om Prakash* , Hitesh Batra, Harpreet Kaur, Pawan K. Sharma, Vijay Sharma, Shiv P. Singh, Robert M. Moriarty
  • *Department of Chemistry, Kurukshetra University, Kurukshetra-136119, India; Fax + 91(17 44)2 02 77
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Publication Date:
31 December 2001 (online)

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Oxidation of anthranilamides, salicylamides and some β-substituted amides with iodobenzene diacetate in methanolic potassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.

hypervalent iodine - 2-benzimidazolones - 2-benzoxazolones - Hofmann rearrangement - heterocycles - cyclization