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Lewis Acid Catalyzed Synthesis of 1‐Aryl‐1,2‐dihydro‐naphtho[1,2‐e][1,3]oxazin‐3‐ones under Solvent Free Conditions: A Mechanistic Approach
Author(s) -
Sharma Mukul,
Manohar Sunny,
Rawat Diwan S.
Publication year - 2012
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.825
Subject(s) - chemistry , lewis acids and bases , catalysis , aryl , solvent , lewis acid catalysis , iodine , medicinal chemistry , organic chemistry , alkyl
Lewis acids catalyzed highly efficient one‐pot three component coupling of β‐naphthol, benzaldehydes and urea to produce 1‐aryl‐1,2‐dihydro‐naphtho[1,2‐e][1,3]oxazin‐3‐one derivatives under solvent free conditions is described. Mechanistic studies confirmed that product formation is possible only at very high temperature (140–150°C) and at lower temperature (90–100°C) formation of 14‐aryl‐14 H ‐dibenzo(a,j)xanthenes was observed. Among the nine Lewis acids screened, iodine, P 2 O 5 and Yb(OTf) 3 are found to be most effective catalyst for this multicomponent reaction.