Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400

Palle V. R. Acharyulu; P. K. Dubey; P. V. V. Prasada Reddy; Thatipally Suresh

doi:10.3998/ark.5550190.0009.b10

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Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400

Palle V. R. Acharyulu; P. K. Dubey; P. V. V. Prasada Reddy; Thatipally Suresh

Volume 2008, Issue 11, pp. 104-111

DOI: http://dx.doi.org/10.3998/ark.5550190.0009.b10

Paper ID: 08-2874GP

Received on 2007-11-06; Accepted on 2008-02-10; Published on 2008-02-29

Permissions: This work is licensed under a Creative Commons Attribution-NonCommercial 3.0 License. Please contact [email protected] to use this work in a way not covered by the license.

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General Papers ARKIVOC 2008 (xi) 104-111 7.3-8.3 (m, 9H, Ar-H). M/z (M +. +1): 322. Anal. Calcd. for (C19H19N3O2) requires: C, 71.01; H, 5.96; N, 13.08; Found: C, 71.05; H, 5.92; N, 13.02%. 2-Morpholin-4-ylmethyl-3-o-tolyl-3H-quinazolin-4-one (5c). IR (KBr) cm-1: 1684. 1H NMR (200MHz, CDCl3): d 2.15 (s, 3H, -CH3), 2.2-2.4 (m, 4H, morpholine), 3.1-3.3 (dd, 2H, -CH2), 3.5-3.6 (m, 4H, morpholine), 7.2-8.3 (m, 8H, Ar-H). M/z (M +. +1): 336. Anal. Calcd. for (C20H21N3O2) requires: C, 71.62; H, 6.31; N, 12.53; Found: C, 71.58; H, 6.26; N, 12.55%. 2-Morpholin-4-ylmethyl-3-(2-trifluoromethyl-phenyl)-3H-quinazolin-4-one (5d). IR (KBr) cm-1: 1678. 1H NMR (200MHz, CDCl3): d 2.2-2.4 (dd, 4H, morpholine), 3.1-3.2 (dd, 2H, -CH2), + 3.6 (q, 4H, morpholine), 7.5-8.3 (m, 8H, Ar-H). M/z (M . +1): 390. Anal. Calcd. for (C20H18F3N3O2) requires: C, 61.69; H, 4.66; N, 10.79 ; Found: C, 61.65; H, 4.62; N, 10.72%. 3-(3-Methoxy-phenyl)-2-(4-oxo-piperidin-1-ylmethyl)-3H-quinazolin-4-one (6a). IR (KBr) cm-1:1670, 1711. 1H NMR (200MHz, CDCl3): d 2.3. (m, 4H, piperidone), 2.6-2.8 (m, 4H, piperidone), 3.4 (s, 2H, -CH2), 3.8 (s, 3H, -OCH3), 6.9-8.3 (m, 8H, Ar-H). M/z (M +. +1): 364. Anal. Calcd. for (C21H21N3O3) requires: C, 69.41, H, 5.82; N, 11.56; Found: C, 69.38; H, 5.80; N, 11.54%. 2-(4-Oxo-piperidin-1-ylmethyl)-3-phenyl-3H-quinazolin-4-one (6b). IR (KBr) cm-1: 1675, 1714. 1H NMR (200MHz, CDCl3): d 2.3 (t, 4H, piperidone), 2.6 (t, 4H, piperidone), 3.4 (s, 2H, - CH2), 7.2-8.3 (m, 9H, Ar-H). M/z (M +. +1): 334. Anal. Calcd. for (C20H19N3 O2) requires: C, 72.05; H, 5.74; N, 12.60; Found: C, 72.01; H, 5.78; N, 12.58%. 2-(4-Oxo-piperidin-1-ylmethyl)-3-o-tolyl-3H-quinazolin-4-one (6c). IR (KBr) cm-1: 1678, 1714: 1H NMR (200MHz, CDCl3): d 2.2 (s, 3H, -CH3), 2.3 (dd, 4H, piperidone), 2.6 (dd, 4H, piperidone), 3.2-3.4 (dd, 2H, -CH2), 7.2-8.3 (m, 8H, Ar-H). M/z (M +. +1): 348. Anal. Calcd. for (C21H21N3O2) requires: C, 72.60, H, 6.09, N, 12.10; Found: C, 72.62; H, 6.01; N, 12.04%. 2-(4-Oxo-piperidin-1-ylmethyl)-3-(2-trifluoromethyl-phenyl)-3H-quinazolin-4-one (6d). IR (KBr) cm-1: 1686, 1717. 1H NMR (200MHz, CDCl3): d 2.3 (m, 4H, piperidone), 2.7-2.9 (m, 4H, piperidone) 3.3 (dd, 2H), 7.5-8.3 (m, 8H, Ar-H). M/z (M +. +1): 402. Anal. Calcd. for (C21H18F3N3O2) requires: C, 62.84; H, 4.52, N, 10.47; Found: C, 62.80; H, 4.46; N, 10.42%. Acknowledgements We are thankful to Dr. H. R. Mohan (Aptuit-Laurus) for his useful discussions in this work. References 1. Merzer, J. D. Angew. Chem. Int Ed. 1998, 37, 2975. 2. Tanaka, T.; Toda, F. Chem. Rev. 2000, 100, 1025. 3. Toda, F. Acc. Chem. Res. 1995, 28, 480. 4. Khodaei, M. M.; Meybodi, F. A.; Rezai, F.; Salehi, P. Synth. Commun. 2001, 31, 2047. ISSN 1551-7012 Page 110 ©ARKAT USA, Inc.

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