One-pot multi-component synthesis of tetrahydroquinazolinones via Biginelli condensation using molecular iodine as a catalyst

Mohsen Abdel-Motaal Gomaa; Abdel-Wahed Rashad Sayed; Ragab Ali Masoud

doi:10.5155/eurjchem.4.4.459-461.821

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Published: Dec 31, 2013

DOI: https://doi.org/10.5155/eurjchem.4.4.459-461.821

Keywords:

Urea, Dimedone, Biginelli reaction, Molecular iodine, Tetrahydroquinazolinone, Tetrahydroquinazolinthione

Section

Short Communication

Issue

Vol. 4 No. 4 (2013): December 2013

Dates

Received 2013-05-03
Accepted 2013-06-09
Published 2013-12-31

Mohsen Abdel-Motaal Gomaa

Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt

Abdel-Wahed Rashad Sayed

Chemistry Department, Faculty of Science, Beni Suef University, 62511 Beni Suef, Egypt

Ragab Ali Masoud

College of Agriculture and Food Sciences, King Faisal University, Al-Hufuf 31982, Saudi Arabia

Abstract

Tetrahydroquinazolinone derivatives were synthesized in moderate to high yields via one‐pot three component Biginelli reaction of dimedone, urea or thiourea and corresponding aromatic aldehydes in the presence of molecular iodine as an efficient catalyst, in ethanol under reflux conditions. This protocol offers several advantages including good yields of products and easy experimental work‐up procedure.

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(1)

Gomaa, M. A.-M.; Sayed, A.-W. R.; Masoud, R. A. One-Pot Multi-Component Synthesis of Tetrahydroquinazolinones via Biginelli Condensation Using Molecular Iodine As a Catalyst. Eur. J. Chem. 2013, 4, 459-461.

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References

[1]. Niralwad, K. S.; Shingate, B. B.; Shingare, M. S. Tetrahedron Lett. 2010, 51, 3616-3618.
http://dx.doi.org/10.1016/j.tetlet.2010.04.118

[2]. Niralwad, K. S.; Shingate, B. B.; Shingare, M. S. J. Chin. Chem. Soc. 2010, 57, 89-92.

[3]. Bandgar, B. P.; More, P. E.; Kamble, V. T.; Totre, J. V. Arkivoc 2008, 15, 1-8.
http://dx.doi.org/10.3998/ark.5550190.0009.f01

[4]. Kidwai, M.; Saxena, S.; Khalilur, R. K.M.; Thukral, S. S. Eur. J. Med. Chem. 2005, 40, 816-819.
http://dx.doi.org/10.1016/j.ejmech.2005.02.009
PMid:16122583

[5]. Yarim, M.; Sarac, S.; Kilic, F. S.; Erol, K. Il Farmaco 2003, 58, 17-24.
http://dx.doi.org/10.1016/S0014-827X(02)00009-5

[6]. Yarim, M.; Sarac, S.; Ertan, M.; Kilic, F. S.; Erol, K. Arzneim. Forsch. 2002, 52, 27-33.
PMid:11838271

[7]. Eynde, J. J. V.; Godin, J.; Mayence, A.; Ma-questiau, A.; Anders, E. Synthesis 1993, 9, 867-869.
http://dx.doi.org/10.1055/s-1993-25958

[8]. Kempter, G.; Ehrlichmann, W.; Plesse, M.; Lehm, H. U. J. Prakt. Chem. 1982, 324, 832-840.
http://dx.doi.org/10.1002/prac.19823240518

[9]. Hassani, Z.;Islami, M. R.; Kalantari, M. Bioorg. Med. Chem. Lett. 2006, 16, 4479-4482.
http://dx.doi.org/10.1016/j.bmcl.2006.06.038
PMid:16806918

[10]. Mobinikhaledia, A.; Foroughifara, N.; Khodaeia, H. Eur. J. Chem. 2010, 1(4), 291-293.
http://dx.doi.org/10.5155/eurjchem.1.4.291-293.108

[11]. Debache, A.; Chouguiat, L.; Boulcina, R.; Carboni, B. The Open Org. Chem. J. 2012, 6, 12-20.

[12]. Walsh, P. J.; Li, H. M.; Parrodi, C. A. A. Chem. Rev. 2007, 107, 2503-2545.
http://dx.doi.org/10.1021/cr0509556
PMid:17530908 PMCid:PMC2525622

[13]. Saxena, I.; Borah, D. C.; Sarma, J. C. Tetrahedron Lett. 2005, 46, 1159-1160.
http://dx.doi.org/10.1016/j.tetlet.2004.12.081

[14]. Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111-9113.
http://dx.doi.org/10.1016/j.tetlet.2004.10.021

[15]. Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C. F. Tetrahedron Lett. 2005, 46, 5771-5774.
http://dx.doi.org/10.1016/j.tetlet.2005.05.148

[16]. Srinivas, K. V. N. S.; Das, B. Synthesis 2004, 13, 2091-2093.

[17]. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243-7247.
http://dx.doi.org/10.1016/S0040-4039(98)01555-X

[18]. Banik, B. K.; Zegrocka, O.; Banik, I.; Hackfeld, L.; Becker, F. F. Tetrahedron Lett. 1999, 40, 6731-6737.
http://dx.doi.org/10.1016/S0040-4039(99)01395-7

[19]. Gomaa, M. A. M. E-J.Chem. 2011, 8(S1), S91-S96.

[20]. Kappe, C. O. Tetrahedron 1993, 49, 6937-6963.
http://dx.doi.org/10.1016/S0040-4020(01)87971-0

[21]. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879-888.
http://dx.doi.org/10.1021/ar000048h
PMid:11123887

[22]. Kantevari, S.; Bantu, R.; Nagarapu, L. Arkivoc 2006, 16, 136-148.

[23]. Shahani, A.; Sarvary, A. Rayan, A. H. Lett. Org. Chem. 2007, 4, 68-71.

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King Faisal University, Al-Hufuf 31982, Saudi Arabia

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