Abstract
The reactive intermediate generated by the addition of alkyl isocyanides to dialkyl acetylenedicarboxylates was trapped by N-formyl urea to produce highly functionalized dihydropyrimidinones in fairly good yields. KEY WORDS : Alkyl isocyanides, Dialkyl acetylenedicarboxylate, N-Formyl urea, Three-component reaction, Dihydropyrimidinones Bull. Chem. Soc. Ethiop. 2017 , 31(2), 345-350. DOI: http://dx.doi.org/10.4314/bcse.v31i2.16
Highlights
The dihydropyrimidinones (DHPMs) have exhibited interesting and multifaceted pharmacological properties such as antitumor, anti-inflammatory, antiviral, antifungal and antibacterial activity [1-3]. These compounds have emerged as potential calcium channel blockers, antihypertensive, α1a-adrenergic antagonists and neuropeptide antagonists [4]
New methods for the synthesis of dihydropyrimidinones have been developed by different groups [6-15]
Isocyanide-based multicomponent reactions (IMCRs) by virtue of their synthetic potential, convergent nature and molecular diversity have attracted much attention because of the advantages that they offer in the field of combinatorial chemistry [21-23]
Summary
The dihydropyrimidinones (DHPMs) have exhibited interesting and multifaceted pharmacological properties such as antitumor, anti-inflammatory, antiviral, antifungal and antibacterial activity [1-3]. Yellow powder, (052 g, 76% yield), mp [153-155] oC; IR (KBr) νmax 3411, 2938, 2855, 1737, 1686, 1440, 1199, 1141, 1023, 953, 708 cm-1; 1H NMR (CDCl3, 300 MHz) δ 9.33 (1H, s, CHO), 8.78 (1H, brs, NH), 6.95 (1H, brs, NH), 5.86 (1H, s, CH), 4.08-4.38 (4H, m, 2OCH2), Bull. Yellow powder (0.63 g, 86 % yield), mp [150-152] oC; IR (KBr) νmax 33430, 2944, 2856, 1738, 1698, 1449, 1370, 1199, 1025, 954, 750 cm-1; 1H NMR (CDCl3, 300 MHz) δ 9.35 (1H, s, CHO), 8.75 (1H, brs, NH), 8.00 (1H, brs, NH), 5.87 (1H, s, CH), 4.03-4.32 (4H, m, 2OCH2), 3.42-3.49 (1H, m, CH), 1.32 (3H, t, J = 7.1 Hz, CH3), 1.25 (3H, t, J = 7.1 Hz, CH3), 1.15-1.46, (10H, m, CH2); 13C NMR (CDCl3, 75 MHz) δ 169.9 (CHO), 167.5 (C=O ester), 160.7 (C=O ester), 151.8 (N2C=O), 149.8 (CN2), 70.7 (C), 61.8 (OCH2), 59.4 (OCH2), 50.2 (CHN), 49.8. C 57.33%, H 7.78%, N 10.64%, calcd. for C19H31N3O6, C 57.41%, H 7.86%,
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