- HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst
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A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.
- Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.
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supporting information
(2020/10/20)
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- Design, Multicomponent Synthesis and Characterization of Diversely Substituted Pyrazolo[1,5-a] Pyrimidine Derivatives
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The synthesis of various heterocyclic compounds using acetoacetanilide[AAA], we have demonstrated that acetoactanilide are versatile intermediate for the synthesis of pyrazolopyrimidine derivatives. Thus, to explore further, we sought that the reaction of various acetoactanilide, an appropriate aldehyde and 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide in the presence of base in isopropyl alcohol could be an effective strategy to furnish the novel pyrazolopyrimidine derivatives. Here we describe the novel synthetic methodology for the fused pyrazolopyrimidines.
- Ghelani, Satish M.,Naliapara, Yogesh T.
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p. 1843 - 1851
(2016/11/23)
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- Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
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Rapid and facileaccess to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. Indian Academy of Sciences.
- Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
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p. 187 - 195
(2014/04/03)
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- Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
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Rapid and facile access to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. [Figure not available: see fulltext.]
- Jaggavarapu, Satyanarayana Reddy,Kamalakaran, Anand Solomon,Jalli, Ventkata Prasad,Gangisetty, Sravan Kumar,Ganesh, Munusswamy Ramanujam,Gaddamanugu, Gopikrishna
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p. 187 - 195
(2016/02/26)
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- Further Reactions of t-Butyl 3-Oxobutanthioate and t-Butyl 4-Diethylphosphono-3-oxobutanthioate: Carbonyl Coupling Reactions, Amination, Use in The Preparation of 3-Acyltetramic Acids and Application to The Total Synthesis of Fuligorubin A.
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Key words: Acyltetramic acid; Phosphonate; Wadsworth-Emmons; Dieckmann cyclisation; Fuligorubin A. Abstract: The use of t-butyl-3-oxobutanthioate (1) and t-butyl 4-diethylphosphono-3-oxobuthanthioate (2) for the preparation of homologated derivatives suitable for amination in the presence of silver(I) trifluoroacetate to afford the corresponding β-ketoamides is discussed.In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products.Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckman cyclisation with tetra-n-butyl ammonium fluoride as the cyclising base.These new reactions were applied to the total synthesis of the polyene 3-acyltetramic acid fuligorubin A.
- Ley, Steven V.,Smith, Stephen C.,Woodward, Peter R.
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p. 1145 - 1174
(2007/10/02)
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- THE USE OF β-KETOTHIOESTERS FOR THE EXCEPTIONALLY MILD PREPARATION OF β-KETOAMIDES
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Transamination of t-butylacetothioacetate derivatives with primary and secondary amines in the presence of silver(I) trifluoroacetate gives high yields of the corresponding β-ketoamides.
- Ley, Steven V.,Woodward, Peter R.
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p. 3019 - 3020
(2007/10/02)
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- DERIVATIVES OF 3,4-DIHYDRO-3-THIOXO-2-QUINOXALINYLACETIC ACID
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Ethyl 3,4-dihydro-4-methyl-3-thioxo-2-quinoxalinylacetate has been prepared by thionation of the 3-oxo derivative.The mechanism is discussed of the reaction of this ester with diethylamine giving the two non-isomerizing ketimine-enamine tautomers and 1,2-
- Toman, Jaromir,Klicnar, Jiri
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p. 419 - 428
(2007/10/02)
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