Silica Sulfuric Acid as a Mild and Efficient Reagent for the Synthesis of 1,4-Diazepine and 1,5-Benzodiazepine Derivatives
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The synthesis of biologically active 1H-1,4-diazepines 4a-d and 3H-1,5-benzodiazepines 5a-d in good yields, from the heterocyclization reaction of 2-(4-methylthio benzenesulfonyl)-1,3-dimethyl/1-methyl-3-phenyl/1,3 diphenyl/1-methyl-3-ethoxy propane-1,3-dione 3a-d with ethylenediamine (EDA) and o-phenylenediamine (o-PDA), respectively, in the presence of silica sulfuric acid (SSA) is described. The novel β-diketones/β-ketoesters 3a-d were synthesized by the condensation reaction of 4 methylthiobenzenesulfonyl chloride 1 with various β-diketones/β-ketoesters 2a-d. All structures of the newly synthesized compounds were elucidated by elemental analysis and spectral studies. The compounds 4a-d and 5a-d have been screened for antimicrobial, antifungal and anthelmintic activity.
Abstract
Silica sulfuric acid (SSA)를 이용하여 ethylenediamine (EDA)과 o-phenylenediamine (o-PDA)을 2-(4-methylthio benzenesulfonyl)-1,3-dimethyl/1-methyl-3-phenyl/1,3-diphenyl/1-methyl-3-ethoxypropane-1,3-dione 3a-d과의 헤테로고리화 반응을 통하여 좋은 생리활성을 나타내는1H-1,4-diazepines 4a-d과 3H-1,5-benzodiazepines 5a-d을 좋은 수율로 합성하였다. 이 반응에서 β-diketones/β-ketoesters 3a-d는 4-methylthiobenzenesulfonyl chloride 1과 다양한 β-diketones/β-ketoesters 2a-d과의 축합반응으로 합성하였으며, 합성한4a-d와 5a-d 화합물들에 대해서 fantimicrobial, antifungal 및anthelmintic 활성을 측정하였다.
참고문헌 (32)
- Landquist, J. K., "In Comprehensive Heterocyclic chemistry Vol. 1", pp.166~ (1984), Pergamon
- Lioyed, D., , J. Chem. Soc, pp.2597~ (1956)
- Keshava Murthy K. S., , Drug Dev. Res, 46(2), pp.155~ (1999)
- Gorlitzer, K., , Arch. Pharm, 328(3), pp.247~ (1995)
- Sprio, V., , Farmaco. Sci, 44(9), pp.809~ (1989)
- Bianchi, M., , Farmaco. Sci, 39(2), pp.162~ (1984)
- Ramajayam, R., , J. Enzyme Inhib. and Med. Chem, 22(6), pp.716~ (2007)
- Insuasty, B., , Eur. J. Med. Chem, 43(9), pp.1955~ (2008)
- DeWald, H. A., , J. Med. Chem, 16(12), pp.1346~ (1973)
- Raboisson, P., , Bioorg. Med. Chem. Lett, 15(7), pp.1857~ (2005)
- Ramnauth, J., , Bioorg .Med. Chem. Lett, 19(18), pp.5359~ (2009)
- DeWald, H. A., , J. Med. Chem, 24(8), pp.982~ (1981)
- De Baun, J. R., "U. S. Patent 3,978,227", ~ (1976)
- Haris, R. C., "U. S. Patent 1,537,757", ~ (1968)
- Ried, W., , Chem. Ber, 92, pp.2902~ (1959)
- Balakrishna, M. S., , Tetrahedron Lett, 12, pp.1127~ (2001)
- Curini, M., , Tetrahedron Lett, 42, pp.3153~ (2001)
- Sabita, G., , Adv. Synth. Catal, 346, pp.921~ (2004)
- Kaboudin, B., , Heterocycles, 55, pp.1443~ (2001)
- Pozaretzi, M., , Tetrahedron Lett, 43, pp.1755~ (2002)
- Reddy, B. M., , Tetrahedron Lett, 44, pp.4447~ (2003)
- Yadav, J. S., , Green Chem, 4, pp.592~ (2002)
- Jarikote, D. V., , Tetrahedron Lett, 44, pp.1835~ (2003)
- De Surya, K., , Tetrahedron Lett, 46, pp.1811~ (2005)
- Wight, A. P., , Chem. Rev, 102, pp.3589~ (2002)
- Shirini, F., , Chin. Chem. Lett, 20(12), pp.1457~ (2009)
- Kumar, R., , J. Chem. Sci, 121, pp.497~ (2009)
- Kumar, R., , ARKIVOC, XIII, pp.142~ (2007)
- Saingar, S., , Med. Chem. Res (2010)
- Salehi, P., , Curr. Org. Chem, 10, pp.2171~ (2006)
- Saundane, A. R., , Indian J. Pharm. Sci, 60, pp.379~ (1998)
- Bagvant, G., , Indian J. Pharm. Sci, 56, pp.80~ (1994)