- N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters
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N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack (VH) adducts with 1,3,5-triazine compunds such as trichloroisocyanuric acid (TCCA) and trichlorotriazine (TCTA) were prepared by replacing classical oxy chlorides POCl3, and SOCl2, which were explored as efficient catalysts for the transesterification of β-ketoesters. The prepared (TCCA/DMF) and (TCTA/DMF) adducts improved greenery of the classical Vilsmeier–Haack reagents (POCl3/DMF), and (SOCl2/DMF), and demonstrated their better efficient catalytic ativity. Reaction times were in the range: 3.5 to 6.5 hr (SOCl2/DMF); 2.8–5.2 hr (POCl3/DMF); 2.5–5.2 hr (TCCA/DMF) and 2.5–5.0 hr (TCTA/DMF) catalytic systems. Ultrasonically (US) assisted protocols with these reagents further reduced the reaction times (two to three times), while microwave assisted (MW) protocols with these reagents were much more effective. The reactions could be completed in only few seconds (less than a minute) in MWassisted protocols as compared to US assited reactions, followed by good product yields.
- Chityala, Yadaiah,Duguta, Govardhan,Kamatala, Chinna Rajanna,Muddam, Bhooshan,Mukka, Satish Kumar
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- Prussian blue as an efficient catalyst for rate accelerations in the transesterification of β-ketoesters
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Prussian blue triggered transesterification of ethylacetoacetate with various alcohols underwent efficiently. The reaction is mild, eco-friendly, and selective with good yields. The proposed reaction pathway depicts the formation of an intermediate by the interaction of β-ketoesters with catalytic site of the Prussian blue, followed by nucleophilic attack of the alcohol at the electrophilic center followed by successive elimination of the proton to give the product. Observed longer reaction times under conventional conditions reduced amazingly under sonication and microwave irradiation followed enhanced yield of products.
- Srinivas,Rajanna,Krishnaiah,Kumar, M. Satish,Reddy, J. Narender
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p. 1212 - 1220
(2014/04/17)
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