An efficient synthesis of 2-benzoxepines from Morita-Baylis-Hillman adducts using heterogeneous recyclable catalysts

Biswanath Das; Anjoy Majhi; Joydeep Banerjee; Nikhil Chowdhury; Harish Holla; Kankipati Harakishore; Upadhayula Suryanarayana Murty

doi:10.1248/cpb.54.403

An efficient synthesis of 2-benzoxepines from Morita-Baylis-Hillman adducts using heterogeneous recyclable catalysts

Chem Pharm Bull (Tokyo). 2006 Mar;54(3):403-5. doi: 10.1248/cpb.54.403.

Authors

Biswanath Das¹, Anjoy Majhi, Joydeep Banerjee, Nikhil Chowdhury, Harish Holla, Kankipati Harakishore, Upadhayula Suryanarayana Murty

Affiliation

¹ Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad, India. [email protected]

PMID: 16508203
DOI: 10.1248/cpb.54.403

Abstract

2-Benzoxepines have efficiently been synthesized from Morita-Baylis-Hillman adducts, alkyl 3-aryl-3-hydroxy-2-methylenepropanoates by treatment with HCHO catalyzed by silica supported perchloric acid (HClO4.SiO2) or Amberlyst-15 in CH2Cl2 under reflux for a short period of time (1.5-2.5 h). The catalyst can be recovered and recycled. The antibacterial properties of the new 2-benzoxepines were studied but no activity was found.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology*
Bacteria / drug effects
Benzoxepins / chemical synthesis*
Benzoxepins / pharmacology*
Catalysis
Chromatography, Thin Layer
Ciprofloxacin / pharmacology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Spectrophotometry, Infrared
Spectroscopy, Fourier Transform Infrared

Substances

Anti-Bacterial Agents
Benzoxepins
Indicators and Reagents
Ciprofloxacin