41377-36-0Relevant academic research and scientific papers
Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate
Layek, Samaresh,Agrahari, Bhumika,Ganguly, Rakesh,Das, Parthasarathi,Pathak, Devendra D.
, (2020/01/25)
Benzoylhydrazone Schiff base–ligated three new ONO pincer–type palladium(II) complexes, [(PdL1(PPh3)] (1), [(PdL2(PPh3)] (2), and [(PdL3(PPh3)] (3), were synthesized by the reaction of the respective ligand, N-(2-hydroxybenzylidene)benzohydrazide (HL1), N-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (HL2), or N-(5-bromo-2-hydroxybenzylidene) benzohydrazide (HL3), with Pd(OAc)2 and PPh3 in methanol and isolated as air-stable reddish-orange crystalline solids in high yields (78%–83%). All three complexes were fully characterized by elemental analysis, Fourier-transform infrared spectroscopy, UV–Visible, 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, and 31P{1H} NMR spectroscopic studies. The molecular structure of all three complexes was established unambiguously by single-crystal X-ray diffraction studies which revealed a distorted square planar geometry of all three complexes. The ONO pincer–type ligands occupied three coordination sites at the palladium, while the fourth site is occupied by the monodentate triphenylphosphine ligand. The catalytic potential of all three complexes was explored in the carbonylative Suzuki coupling of aryl bromides and iodides with arylboronic acids to yield biaryl ketones, using CHCl3 as the source of carbonyl. The reported protocol is convenient and safe as it obviates the use of carbon monoxide (CO) balloons or pressured CO reactors which are otherwise needed for the carbonylation reactions. The methodology has been successfully applied to the synthesis of two antineoplastic drugs, namely, phenstatin and naphthylphenstatin, in good yields (81% and 85%, respectively). Under the optimized reaction conditions, complex 2 exhibited the best catalytic activity in the carbonylative Suzuki couplings. The reported catalysts have wide reaction scope with good functional group tolerance. All catalysts could be retrieved from the reaction after completion and recycled up to three times with insignificant loss in the catalytic activity.
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.
Organocatalytic synthesis of densely functionalized oxa-bridged 2,6-epoxybenzo[: B] [1,5]oxazocine heterocycles
Gurubrahamam, Ramani,Nagaraju, Koppanathi,Chen, Kwunmin
supporting information, p. 6048 - 6051 (2018/06/18)
Metal-free addition of salicylhydrazones to electron deficient internal alkynes catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield oxa-bridged 2,6-epoxybenzo[b][1,5]oxazocine heterocycles was achieved. The demonstrated protocol proceeds through an o-quinone methide formation, aza-Michael addition, stereoselective protonation, enamine promoted aromatization, O,O-acetalization and O,N-aminalization sequence to provide privileged heterocycles in good yields with high diastereoselectivities.
Synthesis of Hydrazide-Containing Chroman-2-ones and Dihydroquinolin-2-ones via Photocatalytic Radical Cascade Reaction of Aroylhydrozones
Zhao, Yu,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information, p. 6304 - 6307 (2016/12/23)
A general and efficient visible light photocatalytic α-amino carbon radical-based cascade reaction of aroylhydrazones has been described. This protocol tolerates a wide array of α-silylamines and aroylhydrazones to afford the corresponding diversely funct
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.
Efficient synthesis of functionalized 1,3-dihydroisobenzofurans from salicylaldehydes: Application to the synthesis of escitalopram
Wang, Peng,Zhang, Rui,Cai, Jin,Chen, Jun-Qing,Ji, Min
, p. 549 - 552 (2014/05/06)
An efficient synthesis of substituted 1,3-dihydroisobenzofurans is developed. In this novel route, o-aroylbenzaldehydes, as key intermediates, can be obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. The mild and general st
SYNERGISTIC FUNGICIDAL COMPOSITIONS INCLUDING HYDRAZONE DERIVATIVES AND COPPER
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Page/Page column 59, (2010/08/08)
The present invention relates to the use of mixtures containing hydrazone compounds and copper for controlling the growth of fungi.
A versatile and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans
Jacq, Jerome,Einhorn, Cathy,Einhorn, Jacques
supporting information; experimental part, p. 3757 - 3760 (2009/07/01)
(Chemical Equation Presented) A convenient, versatile, and regiospecific synthesis of functionalized 1,3-diarylisobenzofurans has been developed. It involves chemoselective addition of arylmagnesium reagents to the aldehyde function of o-aroylbenzaldehydes, themselves readily obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. Various functional groups, including nitro, iodo, or ester functionalities, have thus been positioned with complete regiospecificity on the 1,3-diphenylisobenzofuran backbone.
