Basic alumina supported one-pot synthesis of structurally diverse pyridine/quinolinine-fused novel diazepanium, diazocanium, imidazodilinium and tetrahydro-pyrimidiniums

Tetrahedron Letters

Volumn 52, Issue 14, 2011, Pages 1653-1657

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

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

Basic alumina; Diazepaniums; Diazocaniums; Imidazodiliniums; Microwave; Tetrahydro pyrimidiniums

Indexed keywords

ALUMINUM OXIDE; DIAZEPANIUM; DIAZOCANIUM; IMIDAZODILINIUM; POLYCYCLIC AROMATIC COMPOUND; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SILICA GEL; TETRAHYDROPYRIMIDINIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; PURIFICATION;

EID: 79952360262     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.134     Document Type: Article

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38. General reaction procedure: 3.3 mmol 2-aminopyridine derivatives (1a, 1b) or 8-aminoquinoline (4) and 6 mmol dibromoalkanes or benzylic dibromides (2a-e) were placed in a round bottomed flask (25 ml) and dissolved in minimum amount of chloroform. Basic alumina (0.4 g) was then added to the solution and the organic solvent was then evaporated to dryness under reduced pressure. After fitting the flask with a septum the mixture was subjected to irradiation in a microwave reactor (CEM, Discover, USA) at 90 °C (180 W) for appropriate amount of time (as monitored by TLC). After completion of the reaction the reaction mixture was cooled and methanol was added to it and the slurry was stirred at room temperature for 10 min. The mixture was then vacuum filtered through a sintered glass funnel. The filtrate was then evaporated to dryness under reduced pressure and the residue was purified by flash chromatography to isolate the product. In the recycling experiment the residue obtained after vacuum filtration of the reaction mixture was washed with alkaline water and acetone (2-3 times) and subjected to calcination at 150 °C.
39. + 171.0917; found: 171.0931.