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 | Zendy

Sharma Mukul | Zendy; Manohar Sunny | Zendy; Rawat Diwan S. | Zendy

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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.

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