An improved synthesis of Biginelli-type compounds via phase-transfer catalysis

Tetrahedron Letters

Volumn 50, Issue 24, 2009, Pages 2889-2892

  Ahmed, Bahar ^a   Khan, Riaz A ^b   Habibullah, ^a   Keshari, Manoj ^a  

^a HAMDARD UNIVERSITY   (India)

^b INTEGRAL UNIVERSITY   (India)

Author keywords

3,4 Dihydropyrimidin 2(1H) imine; 3,4 Dihydropyrimidin 2(1H) one; 3,4 Dihydropyrimidin 2(1H) thione; Biginelli reaction; Cyclocondensation; Tetra butyl ammonium bromide (TBAB)

Indexed keywords

3,4 DIHYDROPYRIMIDIN 2(1H) IMINE DERIVATIVE; 3,4 DIHYDROPYRIMIDIN 2(1H) ONE; 3,4 DIHYDROPYRIMIDIN 2(1H) THIONE; ALDEHYDE; DIHYDROPYRIDINE DERIVATIVE; GUANIDINE; TETRABUTYLAMMONIUM; THIOUREA; UNCLASSIFIED DRUG; UREA;

ARTICLE; BIGINELLI REACTION; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PHASE TRANSITION;

TETRA;

EID: 65449190174     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.177     Document Type: Article

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23. General method for synthesis of 5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihyd- ropyrimidin-2(1H)-one, 3,4-dihydropyrimidin-2(1H)-thione, and 3,4-dihydropyrim- idin-2(1H)-imine derivatives (1-17): Benzaldehyde or appropriately substituted corresponding benzaldehyde derivatives (10 mmol), ethyl acetoacetate (10 mmol) and either urea/thiourea or guanidines (10 mmol) were mixed together followed by addition of 10% aqueous KOH (0.5 g in 5 mL water) and catalytic amount of solid tetra-butyl ammonium bromide (0.483 g, 1.5 M) in a 100 mL round-bottomed flask. The reaction mixture was heated with stirring at 100 °C for appropriate time (Table 1). The progress of reaction was monitored by TLC and after completion, the resultant mass was poured into crushed ice and solid obtained was filtered through Buckner funnel, washed with ice-cold water, twice with petroleum-ether, and air-dried over Buckner. The obtained oily material was separated, neutralized with 5% aq HCl, water washed, dried over anhydrous sodium sulphate, and concentrated under vacuo. The solid crude products were recrystallized from ethanol.
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