چاپ صفحه |  صفحه نخست سامانه |  نویسندگان |  اطلاعات تفضیلی |  دانلود مقاله | علوم پزشکی کرمانشاه |
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| کلمات کلیدی | IRON(III) TRIFLUOROACETATE AND TRIFLUOROMETHANESULFONATE: NOVEL AND RECYCLABLE LEWIS ACID CATALYSTS FOR ONE-POT SYNTHESIS OF 3,4-DIHYDROPYRIMIDINONES OR THEIR SULFUR ANALOGUES AND 1,4-DIHYDROPYRIDINES VIA SOLVENT-FREE BIGINELLI AND HANTZSCH CONDENSATION PROTOCOLS Hadi Adibi,a,* and Heshmat Allah Samimib aDepartment of Medicinal Chemistry, School of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah 67149-67346, IR Iran bDepartment of Chemistry, Faculty of Sciences, Guilan University, Rasht 41335-1914, IR Iran hadibi@kums.ac.ir Dihydropyrimidinones (DHPMs) have attracted increasing interest due to their diverse therapeutic and pharmacological properties, such as antiviral, antibacterial, antihypertensive and antitumor effects [1]. The original Biginelli protocol for the preparation of DHPMs consisted of heating a mixture of the three components included β–ketoester, aldehyde and urea in ethanol containing a catalytic amount of HCl [2]. As Biginelli reaction for the synthesis of DHPMs has received renewed attention, during the last decade, several improved procedures have been reported based on metal-catalyzed Biginelli reaction and reviews have also been published [3]. DHP drugs such as nifedipine, nicardipine, amlodipine and others are effective cardiovascular agents for the treatment of hypertension [4]. Starting from Hantzsch protocol [5] more than a century ago, it has been mostly reported that there are a plethora protocols applicable to synthesize a wide range of DHPs [6]. Iron(III) trifluoroacetate [Fe(CF3CO2)3] or trifluoromethanesulfonate [Fe(CF3SO3)3] catalyzes the three component coupling of β-dicarbonyl compounds, aldehydes and urea or thiourea to afford the corresponding 3,4-dihydropyrimidinones or their sulfur analogues under solvent-free conditions. Also, these catalysts were used for one-pot synthesis of 1,4-dihydropyridines via solvent-free Hantzsch reaction. This new protocol allows the recycling of catalysts with no loss in their potency (Scheme 1). Scheme 1. References: [1] Kappe, C. O. Tetrahedron 49, 6937, 1993. [2] Biginelli, P. Gazz. Chim. Ital. 23, 360, 1893. [3] (a) Lu, J.; Yang, B. Q.; Bai, Y. J.; Ma, H. R. Chin. Org. Chem. 21, 640, 2001. (b) Jenner, G. Tetrahedron Lett. 45, 6195, 2004. [4] Reid, J. L.; Meredith, P. A.; Pasanisi, F. J. Cardiovasc. Pharmacol. S18, 7, 1985. [5] Hantzsch, A. Justus Liebigs Ann. Chem. 1, 215, 1882. [6] (a) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 46, 5771, 2005. (b) Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R. Synthesis 55, 2006. (c) Lee, J. H. Tetrahedron Lett. 46, 7329, 2005. (d) Sridhar, R.; Perumal, P. T. Tetrahedron 61, 2465, 2005. (e) Sabitha, G.; Reddy, G. S. K. K.; Reddy, Ch. S.; Yadav, J. S. Tetrahedron Lett. 44, 4129, 2003. |
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