Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides and some beta-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds

Authors
Prakash, O Batra, H Kaur, H Sharma, PK Sharma, V Singh, SP Moriarty, RM
Citation
O. Prakash et al., Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides and some beta-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, SYNTHESIS-S, (4), 2001, pp. 541-543
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
4
Year of publication
2001
Pages
541 - 543
Database
ISI
SICI code
0039-7881(200104):4<541:HIOROA>2.0.ZU;2-8
Abstract
Oxidation of anthranilamides, salicylamides and some beta -substituted amid es with iodobenzene diacetate in methanolic potassium hydroxide led to a ne w and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and rela ted compounds, respectively. The reaction probably occurs via initial Hofma nn-type rearrangement followed by intramolecular cyclization of intermediat e isocyanate.