- An alternate and efficient method for preparation of 2,6-diacetamido-4-formylpyridine for formation of porphyrin appended with hydrogen bonding motifs
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We report here an alternate redesigned five-step synthesis of 2,6-diacetamido-4-formylpyridine. The method described here is more convenient where this aldehyde is prepared in commercially viable quantities from simple and easy-to-use reagents and is a key compound required to prepare 5,10,15,20-Tetrakis(3,5-diacetamido-4-pyridyl)porphyrin (I). This porphyrin can be used as an excellent building block for the construction of supramolecular assemblies and is an interesting compound to study the design, principles, and photonic properties such as the extent of electron and energy transfer.
- Singh, Sunaina,Aggarwal, Amit,Mercier, Phillippe H.,Bhupathiraju, N. V. S. Dinesh K.,Landress, Michael,Hanna, Keroles
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p. 3256 - 3263
(2020/08/05)
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- Parallel iterative solution-phase synthesis of 5-amino-1-aryl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid amide derivatives
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The parallel iterative solution-phase synthesis of 5-amino-1-aryl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid amide derivatives is described. The key intermediate 2,6-bis-aminopyridine-4-carboxylic acid methyl ester was synthesised in a two step procedure in 64% overall yield and elaborated to a variety of triazolopyridine-5-carboxylic acid methyl ester by selective pyridine-N-amination, condensation of the adduct with a wide selection of aldehydes and subsequent cyclisation and oxidation. The desired esters were obtained in yields up to 70%. The final transformation to the amide derivatives was accomplished by application of carefully optimised reaction conditions thus giving access to a library of total 500 triazolopyridine amide derivatives. Iterative synthetic cycles (12-48 library members each) allowing for maximal flexibility in chemistry and maximal efficiency in in vitro biological activity optimisation guided by molecular modelling efforts constitute a synergistic procedure for rapid lead optimisation.
- Brodbeck, Bernd,Püllmann, Bernd,Schmitt, Sébastien,Nettekoven, Matthias
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p. 1675 - 1678
(2007/10/03)
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