Vanadium(III) chloride catalyzed Biginelli condensation: Solution phase library generation of dihydropyrimidin-(2H)-ones

Tetrahedron Letters

Volumn 44, Issue 34, 2003, Pages 6497-6499

  Sabitha, Gowravaram ^a   Reddy, G S Kiran Kumar ^a   Reddy, K Bhaskar ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Biginelli condensation; Dihydropyrimidin 2(1H) ones; Parallel synthesis; VCl3

Indexed keywords

BETA OXOCARBOXYLIC ACID ESTER; CHLORIDE; ESTER DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; POLYMERIZATION; SYNTHESIS;

EID: 0043199389     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01564-8     Document Type: Article

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34. The table top organic synthesizer 'Carousel' stirring hot plate was used. The 48 compounds were synthesized in 4 operations, each time 12 reactions were conducted.
35. Typical general experimental procedure: A solution of an aldehyde (4.7 mmol), β-dicarbonyl compound (4.7 mmol) and urea or thiourea (7 mmol) in acetonitrile (10 ml) was heated under reflux in the presence of a catalytic amount of vanadium(III) chloride (10 mol%) for 2 h (TLC) (1-12 samples placed in a multiple synthesizer). The reaction mixture was then poured onto crushed ice and the solid product separated was filtered and recrystallized. The same procedure was repeated 3 more times by placing 12 samples at a time in a multiple synthesizer to provide a 48 compound library of dihydropyrimidin-(2H)-ones.
36. 3: C, 70.58; H, 4.61; N, 9.15. Found C, 70.75; H, 4.45; N, 8.95.