ORGANIC SPECTROSCOPY INTERNATIONAL: 6a-0

Indian Journal of Pharmaceutical Sciences

Year : 2010 | Volume : 72 | Issue : 5 | Page : 613-620

Patel N B, Patel H R. Synthesis and antibacterial and antifungal studies of novel nitrogen containing heterocycles from 5-Ethylpyridin-2-ethanol. Indian J Pharm Sci [serial online] 2010 [cited 2015 Apr 21];72:613-20. Available from: http://www.ijpsonline.com/text.asp?2010/72/5/613/78531

Department of Chemistry, Veer Narmad South Gujarat University, Surat-395 007, India

A novel series of chalcones, pyrimidines and imidazolinone is described; chalcones (4a-o) were prepared from the lead molecule 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde. Pyrimidine (5a-o) derivatives were prepared from the reaction of chalcones and guanidine nitrate in alkali media. Imidazolinones (6a-o) were synthesized from reaction of pyrimidine and oxazolone derivatives (prepared by Erlenmeyer azlactone synthesis). The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, ¹ H and ¹³ C NMR spectral data. All the products were screened against different strains of bacteria and fungi. Most of these compounds showed better inhibitory activity in comparison to the standard drugs.

http://www.ijpsonline.com/article.asp?issn=0250-474X;year=2010;volume=72;issue=5;spage=613;epage=620;aulast=Patel

1-(4-(2,4-dichloro-5-fluorophenyl)-6-(4-(2-(5-ethylpyridin-2-yl)ethoxy)phenyl)pyrimidin-2-yl)-4-(4-fluorobenzylidene)-2-phenyl-1H-imidazol-5(4H)-one (6a):

Brown solid, m.p. 110-112°, yield 56%, R _f : 0.60;

IR (KBr, cm ^-1 ) ν: 3062 (Ar-H), 2953, 2833 (-CH₂ - ), 1795 (-C=O of imidazolinone), 1654 (-C=N imidazolinone), 1612 (-C=N of pyrimidine), 1222, 1036 (C-O-C), 972 (C-F), 743 (C-Cl).

¹ H NMR (CDCl ₃ , 400 MHz) δ(ppm): 1.17 (t, 3H, -CH ₃ ), 2.35(s, 3H, -CH ₃ ), 2.51 (q, 2H, -CH ₂ ), 3.22 (t, 2H, -CH ₂ ), 4.33 (t, 2H, -CH ₂ -O), 7.05-7.55 (m, 16H, Ar-H), 7.31 (s, 1H, -CH), 7.39-8.30 (m, 3H, pyridine-H), 7.81 (s, 1H, pyrimidine-H).

¹³ C NMR (100 MHz, CDCl ₃ ) δ(ppm): 170.4(C ₃₁ ), 165.3(C ₁₉ ), 164.5(C ₃₄ ), 163.1(C ₁₇ ), 161.0(C ₂₁ ), 126.3-135.5 (C ₃₆ -C ₄₁ ), 126.3-130.5 (C ₄₂ -C ₄₇ ), 122.0-157.3 (C ₂ -C ₆ ), 118.7-161.4 (C ₂₃ -C ₂₈ ), 115.0-157.3 (C ₁₁ -C ₁₆ ), 108.5 (C ₃₅ ), 103.3 (C ₂₂ ), 67.2 (C ₁₀ ), 37.3 (C ₉ ), 25.4 (C ₇ ), 15.3 (C ₈ ).

Anal. calcd for C ₄₁ H ₂₉ N ₅ O ₂ Cl ₂ F ₂: C 67.22, H 3.99, N 9.56; found C 67.20, H 3.95, N 9.54.

Department of chemistry, veer narmad south gujarat university, surat, India