Reaction between tert-butyl isocyanide, dialkyl acetylenedicarboxylates, and aromatic carboxylic acids: an efficient method for the synthesis of dialkyl (E)-2-{[benzoyl(tert-butyl)amino]carbonyl}-2-butenedioate derivatives (original) (raw)
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Synthesis of the BEAC 4 ND 4 Ionophore from pt-Butylcalix [ 4 ] arene Carboxylic Acid H )
2021
Article history: Received: 27th May 2020 Revised: 9th November 2020 Accepted: 29th December 2020 Online: 31st January 2021 The BEAC4ND4 ionophore has been successfully synthesized from p-tbutylcalix[4]arene carboxylic acid. The BEAC4ND4 ionophore was obtained in two steps of the synthesis reaction. The first step is the chlorination reaction of p-t-butylcalix[4]arene carboxylic acid with thionyl chloride in dry benzene solvent.The chlorination reaction product is p-t-butylcalix[4]arene acyl chloride in the form of the light brown viscous liquid with a yield of 78.25% and TLC (Si02, CH3OH: CH2CI2 = 1: 1 v/v, Rf = 0.65). The second step is the amidation reaction of ethyl 2-aminoacetate with p-t-butylcalix[4]arene acyl chloride in dry tetrahydrofuran solvent. The product of the amidation reaction is p-tbutylcalix[4]arene ethylesteramide or the BEAC4ND4 ionophore in the form of a white solid with the yield of 75.22%, a melting point of 3i4-3i6°C, and TLC (Si02, CH3OH: CH2CI2 = 1: 1v/v, ...
Synthesis of the BEAC4ND4 Ionophore from p-t-Butylcalix[4]arene Carboxylic Acid
Jurnal Kimia Sains dan Aplikasi
The BEAC4ND4 ionophore has been successfully synthesized from p-t-butylcalix[4]arene carboxylic acid. The BEAC4ND4 ionophore was obtained in two steps of the synthesis reaction. The first step is the chlorination reaction of p-t-butylcalix[4]arene carboxylic acid with thionyl chloride in dry benzene solvent. The chlorination reaction product is p-t-butylcalix[4]arene acyl chloride in the form of the light brown viscous liquid with a yield of 78.25% and TLC (SiO2, CH3OH: CH2Cl2 = 1: 1 v/v, Rf = 0.65). The second step is the amidation reaction of ethyl 2-aminoacetate with p-t-butylcalix[4]arene acyl chloride in dry tetrahydrofuran solvent. The product of the amidation reaction is p-t-butylcalix[4]arene ethylesteramide or the BEAC4ND4 ionophore in the form of a white solid with the yield of 75.22%, a melting point of 314-316°C, and TLC (SiO2, CH3OH: CH2Cl2 = 1: 1 v/v, Rf = 0.75).
Monatshefte Fur Chemie, 2010
Abstract Isocyanides, dialkyl acetylenedicarboxylates, and non-cyclic anhydrides, for example acetic anhydride or benzoic anhydride, react in one-pot to afford 2,5-diaminofuran derivatives and dialkyl (E)-2-[(N-acyl-N-alkylamino)carbonyl]-2-butenedioates in fairly good yields at room temperature. Graphical abstract
Synthetic Communications
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Ring-substituted imidazoles as a new class of anti-tuberculosis agents
European Journal of Medicinal Chemistry, 2004
We describe in vitro anti-Mycobacterium tuberculosis activities of ring-substituted-1H-imidazole-4-carboxylic acid derivatives (1-6), and 3-(2-alkyl-1H-imidazol-4-yl)-propionic acid derivatives (7-13) against drug-sensitive and drug-resistant M. tuberculosis H37Rv strains. The most effective analogues, 2f (R=R 1 =c-C 5 H 9 ), and 2h (R=R 1 =c-C 6 H 11 ) have produced >90% inhibition at a concentration of <6.25 µg/ml in the drug-sensitive screen. Upon further evaluation against drug-resistant strains, both analogues 2f and 2h produced an MIC value of 25.0 µg/ml. The observation of significant anti-tuberculosis activity in some of these analogues describes the discovery of novel ring-substituted-1Himidazole-4-carboxylic acid ethyl esters as a new class of anti-tuberculosis agents.
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