115695-40-4Relevant articles and documents
Structural investigations of aroylhydrazones derived from nicotinic acid hydrazide in solid state and in solution
Gali?, Nives,Brodanac, Ivan,Kontrec, Darko,Miljani?, Sne?ana
, p. 263 - 270 (2013)
Structural forms of aroylhydrazones derived from nicotinic acid hydrazide have been studied in the solid state by FT-IR spectroscopy and in solution by NMR, UV-Vis and ATR spectroscopy. The studied compounds were N′-benzylidene-3-pyridinecarbohydrazide (1), N′-(2,4- dihydroxyphenylmethylidene)-3-pyridinecarbohydrazide (2), N′-(5-chloro-2- hydroxyphenylmethylidene)-3-pyridinecarbohydrazide (3), and N′-(3,5- dichloro-2-hydroxymethoxyphenylmethylidene)-3-pyridinecarbohydrazide (4). The compound 1 adopted the most stable ketoamine form (form I, CONHNC) in the solid state as well as in various organic solvents. In mixtures of organic solvents with water the UV-Vis and ATR spectra implied intermolecular hydrogen bonding of 1 with water molecules. The presence of both tautomeric forms I and II (form II, COHNNC) was proposed for the solid substance and highly concentrated solutions of 2, whereas form I was detected as the predominant one in diluted solutions. For compounds 3 and 4 a coexistence of forms I and III (form III, CONHNHCCCO) was noticed in the solid state and in polar protic organic solvents. The conversion to form III was induced by increasing the water content in the solvent mixtures. This process was the most pronounced for compound 4. When exposed to daylight, an appearance of a new band was observed during time in the UV-Vis spectrum of 4 in organic solvent/water 1/1 mixtures, which implied that tautomeric interconversion was most likely followed by E/Z isomerisation.
BF3-Etherate-catalyzed tandem reaction of 2-formylarylketones with electron-rich arenes/heteroarenes: An assembly of isobenzofurans
Mishra, Pawan K.,Kumar, Ankit,Verma, Akhilesh K.
supporting information, p. 6122 - 6125 (2020/06/18)
An efficient and BF3·Et2O-catalyzed chemoselective synthesis of diversified 1,3-diarylisobenzofuran in a high yield has been described. The reaction proceeds through sequential hydroarylation-cyclization between 2-formylarylketones and electron-rich arenes/heteroarenes. Advantageous features of the developed methodology include operational simplicity, a broad substrate scope, and applicability towards gram scale synthesis. The utility of isobenzofuran derivatives as the diene was extended to the synthesis of [4+2] cyclo-adducts with DMAD and the synthesis of 1,2-dicarbonylarenes in good yields.
Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides
Backes, Gregory L.,Neumann, Donna M.,Jursic, Branko S.
, p. 4629 - 4636 (2014/11/08)
Efficient synthetic procedures for the preparation of acid hydrazines and hydrazides were developed by converting the corresponding carboxylic acid into the methyl ester catalyzed by Amberlyst-15, followed by a reaction with hydrazine monohydrate. Sulfohydrazides were prepared from the corresponding sulfonyl chlorides and hydrazine monohydrate. Both of these group of compounds were condensed with substituted salicylaldehydes using gradient concentration methods that generated a large library of hydrazone, hydrazide and sulfohydrazide analogs. Antifungal activity of the prepared analogs showed that salicylaldehyde hydrazones and hydrazides are potent inhibitors of fungal growth with little to no mammalian cell toxicity, making these analogs promising new targets for future therapeutic development.
