An Efficient Protocol for the One Pot Synthesis of Pyranopyrazoles in Aqueous Medium using Triethanolamine as a Catalyst
Journal Title: Archives of Organic and Inorganic Chemical Sciences - Year 2018, Vol 3, Issue 1
Abstract
The present scenario for organic synthesis indicates the crave for green and economical synthesis of organic compounds. One of it is multi component synthesis. Strecker’s synthesis for amino acids was the first report on multi component reaction [1]. Last few decades show large development in it. The main aim of such reactions is to fasten the reaction rate by reducing number of steps involved and eventually increase the yield of reaction. In this context to achieve great efficiency catalysts are employed. Catalysts such as Nano α-Al2O3 supported ammonium dihydrogenphosphate [2], tungstate sulfuric acid [3], Fe3-xTixO4@SO3H nanoparticles [4], nano-titania sulfuric acid (15-nm TSA) [5], nanostructured MgO [6], H14[NAP5W30O110] [7] and ZnO Nanoparticles [8].Organic catalysts such as Triethylamine [9] DABCO [10], Trishydroxymethyl aminomethane [11] are also reported in various organic transformations. Triethanolamine contains basic tertiary amine and primary alcoholic part (Figure 1). It is used for activation of both CO2 and epoxides to convert them in to cyclic carbonates [12]. It is also reported as a legend for copper catalyzed hydroxylation of aryl halides in aqueous medium [13]. It is used as aqueous solvent for controllable preparation of ZnO nano flowers in sol gel technique [14]. Its aqueous solution is reported as electrolyte in CO2 Photo electro-conversion catalyzed by Cu- Doped Graphene-Titania Catalyst [15]. Also it is found to increase the rate of oxidation of mesitylene catalyzed by cobalt bromide [16]. It is used as sacrificial electron donor in photocatalytic system [17]. Furthermore; it improved the catalytic performance of CuBr/ PMDETA in the atom transfer radical polymerization [18]. It is also used as phase transfer catalyst for synthesis of 1-(arylsulfonyl) aryl/heterylmethanes [19]. It is used as medium for synthesis of 3-substituted coumarins using L-proline as a catalyst [20]. It is reported as catalyst in 10 mol% for synthesis of 2-amino-3-cyano- 4H-pyran derivatives under ultrasound irradiation at 600C [21]. Synthesis of substituted pyrano-[2,3-d]-pyrimidines via one-pot three-component condensation of aromatic aldehydes, malononitrile and barbituric acid or 2-thiobarbituric acid using trace amounts of ionic liquid (choline chloride.ZnCl2) and triethanolamine (0.1Mol%) at 75°C with stirring and under ultrasound irradiation [22] is also reported in literature. Herein we successfully attempted a fast and simple protocol for the synthesis of 6-amino-1,4-dihydro-4-substituted-3-methylpyrano [2,3-c]- pyrazole-5-carbonitrile by the one pot three component reaction of aromatic aldehyde, malononitrile and 3-methyl-1H-pyrazol-5(4H)- one using triethanolamine as a catalyst [23].
Authors and Affiliations
Jayant P Sonar, Sandeep D Pardeshi, Shrikant A Dokhe, Ashok M Zine, Rajendra P Pawar, Shivaji N Thore
Keywords
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- EP ID EP603531
- DOI 10.32474/AOICS.2018.03.000155
- Views 91
- Downloads 0
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