Abstract
A variety of quinazolinones are readily prepared via one-pot three-component reaction in good to excellent yields. The desired products were obtained from the reaction of dimedone, various aldehydes with 2-aminobenzimidazole or 3-amino-1,2,4-triazole under mild reaction conditions using p-toluenesulfonic acid monohydrate as effective catalyst in acetonitrile as solvent. Starting from the corresponding available materials, this friendly and environmentally free-metal procedure has been successfully extended to the synthesis of triazoloquinazolinones and benzimidazoquinazolinones. The salient advantages of this method are mild reaction conditions, nontoxic and inexpensive catalyst, environmentally benign, high to excellent yields, shorter reaction times, easy operation, and no column chromatographic separation.
Graphical abstract
Similar content being viewed by others
References
Lebel H, Ladjel C, Brethous L (2007) J Am Chem Soc 129:13321
Seigal BA, Fajardo C, Snapper ML (2005) J Am Chem Soc 127:16329
Fogg DE, dos Santos EN (2004) Coord Chem Rev 248:2365
Ajamian A, Gleason JL (2004) Angew Chem Int Ed 43:3754
Pokhodylo NT, Matiychuk VS, Obushak MD (2009) J Comb Chem 11:481
Domling A, Ugi I (2000) Angew Chem Int Ed 39:3168
Shaabani A, Seyyedhamzeh M, Maleki A, Behnam M, Rezazadeh F (2009) Tetrahedron Lett 50:2911
Gilchrist TL (1998) Heterocyclic chemistry, 3rd edn. Addison-Wesley Longman, England
Lednicer D (1998) Strategies for organic drugs synthesis and design. Wiley & Sons, New York
Gujaral ML, Saxena PN, Tiwari RS (1955) Indian J Med Res 43:637
Ram VJ, Srimal RC, Kushwaha DS, Mishra L (1990) J Prakt Chem 332:629
Mukerji DD, Nautiyal SR, Prasad GR, Dhawan BN (1980) Indian J Med Res 71:480
Glasser AC, Diamond L, Combs G (1971) J Pharm Sci 60:127
Tani T, Yamada Y, Ochiai T, Ishida R, Inoue I, Oine T (1979) Chem Pharm Bull 27:2675
Reif E, Ericson RJ (1972) 2-(1-Naphthyl)-2,3-dihydro-4(1H)-quinazolinones. German Patent DE 2,118,683. Chem Abstr 76:72546
Ram VJ, Gael A, Verma M, Kanl IB, Kapil A (1994) Bioorg Med Chem Lett 4:2087
Alagarsamy V, Solomon VR, Murugan M (2007) Bioorg Med Chem 15:4009
Alagarsamy V, Venkatesaperumal R, Vijayakumar S, Angayarkanni T, Pounammal P, Senthilganesh S, Kandeeban S (2002) Pharm 57:306
Alagarsamy V (2004) Pharm 59:753
Liu K-C, Hu M-K (1986) Arch Pharm 319:188
Garcia JD, Somanathan R, Rivero IA, Aguirre G, Hellberg LH (2000) Synth Commun 30:2707
Alagarsamy V, Pathak US (2007) Bioorg Med Chem 15:3457
Alagarsamy V, Murugananthan G, Venkateshperumal R (2003) Biol Pharm Bull 26:1711
Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43:4479
Alagarsamy V, Revathi R, Meena S, Ramaseshu KV, Rajasekaran S, De Clercq E (2004) Indian J Pharm Sci 66:459
Puligoundla RG, Karnakanti S, Bantu R, Kommu N, Kondra SB, Nagarapu L (2013) Tetrahedron Lett 54:2480
Krishnamurthy G, Jagannath KV (2013) J Chem Sci 125:807
Heravi MM, Ranjbar L, Derikvand F, Alimadadi B, Oskooie HA, Bamoharram FF (2008) Mol Divers 12:181
Lipson VV, Desenko SM, Shishkina SV, Shirobokova MG, Shishkin OV, Orlov VD (2003) Chem Heterocycl Compd 39:1041
Lipson VV, Desenko SM, Shirobokova MG, Borodina VV (2003) Chem Heterocycl Compd 39:1213
Chandrasekhar S, Johny K, Reddy CR (2009) Tetrahedron Asymmetry 20:1742
Khalafi-Nezhad A, Parhami A, Zare A, Moosavi-Zare AR, Hasaninejad A, Panahi F (2008) Synthesis 4:617
Dekamin MG, Sagheb-Asl S, Naimi-Jamal MR (2009) Tetrahedron Lett 50:4063
Shaabani A, Maleki A, Mofakham H, Moghimi-Rad J (2008) J Org Chem 73:3925
Shaabani A, Maleki A, Moghimi-Rad J (2007) J Org Chem 72:6309
Shaabani A, Seyyedhamzeh M, Maleki A, Bahnam M (2009) Tetrahedron Lett 50:635
Mousavi MR, Hazeri N, Maghsoodlou MT, Salahi S, Habibi-Khorassani SM (2013) Chin Chem Lett 24:411
Lashkari M, Maghsoodlou MT, Hazeri N, Habibi-Khorassani SM, Sajadikhah SS, Doostmohamadi R (2013) Synth Commun 43:635
Sajadikhah SS, Maghsoodlou MT, Hazeri N, Habibi-Khorassani SM, Shams-Najafi SJ (2012) Monatsh Chem 143:939
Shaaban MR (2008) J Fluorine Chem 129:1156
Shaabani A, Rahmati A, Naderi S (2005) Bioorg Med Chem Lett 15:5553
Acknowledgments
Financial support from the Research Council of the University of Sistan and Baluchestan is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mousavi, M.R., Maghsoodlou, M.T. Catalytic systems containing p-toluenesulfonic acid monohydrate catalyzed the synthesis of triazoloquinazolinone and benzimidazoquinazolinone derivatives. Monatsh Chem 145, 1967–1973 (2014). https://doi.org/10.1007/s00706-014-1273-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-014-1273-y