Facile synthesis of 6,6,8,6,6-ring fused pentacyclic heterocycles: annelation of quinolines to quinoxalines under PTC condition

Tetrahedron Letters

Volumn 50, Issue 32, 2009, Pages 4619-4623

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

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

Pentacyclic quinolone; Phase transfer catalysis; Quinolono quinoxaline

Indexed keywords

OXAZOCINE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; QUINOXALINE DERIVATIVE;

ARTICLE; CATALYSIS; ONE POT SYNTHESIS;

EID: 67449088254     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.103     Document Type: Article

References (21)

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19. General reaction procedure for the Synthesis of fused penta cyclic quinolinium cations (4a-d): Appropriate amount of 8-hydroxyquinoline derivatives (3a-d) (3.3 mmol) were dissolved in 50 mL of dichloromethane in a 250 mL RB flask followed by the addition of 50 mL of 10% aqueous NaOH solution, and were stirred at room temperature for about 30 min. Quinoxaline dibromides (2a-b) (10 mmol, 1:3 ratio with respect to the substrate) was added successively to the stirred solution and stirring continued for 10 min. Finally, a catalytic amount of tetra butyl ammonium bromide (phase transfer catalyst) (322.4 mg, 1 mmol) was added to the solution and the reaction mixture was stirred at room temperature. During the course of reaction, TLC was performed after every 1 h to monitor the progress of the reaction and after 4 h the reaction was stopped for isolation intermediate quinolinium only. Then the contents of the reaction mixture were poured to a separating funnel; the organic layer was separated followed by extraction of the aqueous layer with dichloromethane (3 × 25 mL). The entire aqueous layer was further extracted with n-butanol (50 ml) for collecting the rest amount of compounds. Then, all the organic layers were mixed together, washed thoroughly with water until free from alkali, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over silica gel (100-200 mesh), eluted with a mixture of chloroform-methanol in different ratios yielded the respective fused quinolinium cations (4a-d).General reaction procedure for the synthesis of fused penta cyclic quinolones (5a-h): Following similar protocols as for quinolinium cations (4a-d) the reaction was continued for further time period. TLC studies revealed that the conversion of quinolinium cations to quinolones used to take 12-16 h for completion of the reaction. The content of the reaction mixture was then worked up as was done for the quinolinium cations. The chromatographic separation was carried out over silica gel (100-200 mesh), eluted with a mixture of petroleum ether and chloroform in different ratios yielded the respective fused quinolones (5a-h).
20. +; found 366.1193.
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