Amberlite IRA 402(OH): an efficient mediator for the exclusive synthesis of fused tricyclic oxaza quinolinium salts

Tetrahedron Letters

Volumn 51, Issue 24, 2010, Pages 3200-3204

  Paira, Rupankar ^a   Paira, Priyankar ^a   Maity, Arindam ^a   Mondal, Shyamal ^a   Hazra, Abhijit ^a   Sahu, Krishnendu B ^a   Naskar, Subhendu ^a   Saha, Pritam ^a   Banerjee, Maitreyee ^a   Mondal, Nirup B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

Amberlite IRA 402(OH); Fused quinolinium; Reaction in water

Indexed keywords

POLACRILIN; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; PHASE SEPARATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 77953122072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.034     Document Type: Article

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42. (a) General reaction procedure for the synthesis of fused tricyclic quinolinium bromides (3-6 a-d): Appropriate amount (3.3 mmol) of 8-hydroxyquinoline derivatives (1a-e) was taken in 50 mL of water in a 250 mL RB flask under inert atmosphere, 400 mg of Amberlite IRA 402 (OH) was added (after rinsing the resin properly with methanol) and the mixture was stirred at 30-40 °C till dissolution of the substrate. Then 10 mmol (1:3 molar ratios with respect to the substrate) of dibromo alkane (2a-f) was added to the stirred solution of the reaction mixture and the stirring was continued for 30 min. The flask was placed in an oil bath and the stirring was continued for appropriate time at 80 °C. After completion of the reaction, the resin was recovered by simple filtration, thoroughly washed with ethanol and then with alkaline water. Finally it was dried at 80 °C under reduced pressure for 2 h and reused for subsequent runs. Then the filtrate was evaporated to dryness in a rotary evaporator under reduced pressure and the residue was crystallized from methanol, which yielded the respective fused quinolinium bromides (3a-d, 4a-e, 5a-d). In case of oxazoninoquinoliniums (6a-d) the residue obtained after evaporation of the filtrate was subjected to dianion column chromatography and the products were eluted with water and finally crystallized from methanol.
43. +; found 373.9811.