1128-86-5Relevant academic research and scientific papers
Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with 1,3-dibromopropyne, 2-propynyl bromide, and allyl bromide
Nakhmanovich,Karnaukhova,Larina,Ushakov,Lopyrev
, p. 1561 - 1564 (2003)
Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with 1,3-dibromopropyne in MeOH at 50°C afforded 2-phenyl(heteryl)-6- bromomethylidene-4,4-dimethyl-5H-1,3,4-oxadiazinium bromides. Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with
Acidities of Carboxamides, Hydroxamic Acids, Carbohydrazides, Benzenesulfonamides, and Benzenesulfonohydrazides in DMSO Solution
Bordwell, F. G.,Fried, Herbert E.,Hughes, David L.,Lynch, Tsuei-Yun,Satish, A. V.,Whang, Young E.
, p. 3330 - 3336 (1990)
A comparison of acidities of six series of analogous oxygen, nitrogen, and carbon acids in dimethyl sulfoxide (DMSO) solution and the gas phase has shown that the element effect usually causes nitrogen acids to be more acidic than their carbon acid counte
Studies of the structure, amidicity, and reactivity of n-chlorohydroxamic esters and n-chloro-β,β-dialkylhydrazides: Anomeric amides with low resonance energies
Glover, Stephen A.,Rosser, Adam A.,Spence, Robert M.
, p. 1344 - 1352 (2014)
Density functional calculations have been carried out to determine the properties of the title anomeric amides. At the B3LYP/6-31G(d) level, N-chloro-N-methoxyacetamide 8a is computed to be strongly pyramidal at nitrogen with a long amide bond that is unt
Dealkylation of Some Hydrazinium Salts bearing ω-Haloalkyl Substituents by Diazacrown Ethers
Tsuchiya, Shinji,Seno, Manabu
, p. 1679 - 1680 (1993)
The reactions of some hydrazinium salts bearing ω-haloalkyl substituents with diazacrown ethers gave the hydrazine derivatives and N-monoalkylated diazacrown ether salts; dealkylation of the hydrazinium salts occurred.
Synthesis of multi-substituted 1,2,4-triazoles utilising the ambiphilic reactivity of hydrazones
Matsuzaki, Haruo,Takeda, Norihiko,Yasui, Motohiro,Okazaki, Mayuko,Suzuki, Seishin,Ueda, Masafumi
supporting information, p. 12187 - 12190 (2021/11/30)
The synthesis of N-alkyl-1H-1,2,4-triazoles from N,N-dialkylhydrazones and nitriles via formal [3+2] cycloaddition including the C-chlorination/nucleophilic addition/cyclisation/dealkylation sequence was developed. This sequential reaction utilising the in situ generation of hydrazonoyl chloride based on the ambiphilic reactivity of hydrazones afforded a variety of multi-substituted N-alkyl-triazoles in high yields. The synthetic utility of multi-substituted triazoles was also demonstrated by further transformations.
Ruthenium-Catalyzed Three-Component Alkylation: A Tandem Approach to the Synthesis of Nonsymmetric N,N-Dialkyl Acyl Hydrazides with Alcohols
Bettoni, Léo,Joly, Nicolas,Lohier, Jean-Fran?ois,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc
supporting information, p. 4009 - 4017 (2021/07/02)
The borrowing hydrogen strategy has been applied in the synthesis of nonsymmetric N,N-dialkylated acyl hydrazides via a tandem three-component reaction catalyzed by a phosphine free diaminocyclopentadienone ruthenium tricarbonyl complex. This strategy represents the first direct one-pot approach to nonsymmetric functionalized acyl hydrazides. Different aromatic acyl hydrazides underwent dialkylation with a variety of primary or secondary alcohols and methanol or ethanol as alkylating agents in mild reaction conditions and good yields. Deuterium labelling experiments suggested that the primary or secondary alcohol was the hydrogen source in this tandem process. DFT calculations show that the combination of the tandem mixed product cannot be perfectly explained neither structurally nor electronically, but might be dependent of the physical state of the aldehyde or ketone intermediate (gaz vs. liquid) at the reaction temperature. (Figure presented.).
Phosphine-free ruthenium complex-catalyzed synthesis of mono- Or dialkylated acyl hydrazides via the borrowing hydrogen strategy
Joly, Nicolas,Bettoni, Léo,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc
, p. 6813 - 6825 (2021/05/29)
Herein, we report a diaminocyclopentadienone ruthenium tricarbonyl complex-catalyzed synthesis of mono- or dialkylated acyl hydrazide compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary alcohols as alkylating reagents. Deuterium labeling experiments confirm that the alcohols were the hydride source in this cascade process. Density functional theory (DFT) calculations unveil the origin and the threshold between the mono- and dialkylation.
N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation
Saito, Masato,Kawamata, Yu,Meanwell, Michael,Navratil, Rafael,Chiodi, Debora,Carlson, Ethan,Hu, Pengfei,Chen, Longrui,Udyavara, Sagar,Kingston, Cian,Tanwar, Mayank,Tyagi, Sameer,McKillican, Bruce P.,Gichinga, Moses G.,Schmidt, Michael A.,Eastgate, Martin D.,Lamberto, Massimiliano,He, Chi,Tang, Tianhua,Malapit, Christian A.,Sigman, Matthew S.,Minteer, Shelley D.,Neurock, Matthew,Baran, Phil S.
supporting information, p. 7859 - 7867 (2021/05/26)
The site-specific oxidation of strong C(sp3)-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp3)-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.
Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols
Thiyagarajan, Subramanian,Gunanathan, Chidambaram
supporting information, p. 6617 - 6622 (2020/09/02)
Herein, direct N,N-dialkylation of acylhydrazides using alcohols is reported. This catalytic protocol provides one-pot synthesis of both symmetrical and unsymmetrical N,N-disubstituted acylhydrazides using an assortment of primary and secondary alcohols w
Synthesis of N′-propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs) and evaluation of their impact on activities of HDACs and replication of hepatitis C virus (HCV)
Kozlov, Maxim V.,Konduktorov, Konstantin A.,Shcherbakova, Anastasia S.,Kochetkov, Sergey N.
supporting information, p. 2369 - 2374 (2019/06/17)
N′-Propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs), including tubastatin A, vorinostat and belinostat, were synthesized. All prepared compounds inhibited HDAC1/2/3, but not HDAC6, except for one hydrazide analog of HDAC4/5/7 inhibitor that was completely inactive. A novel 4-substituted derivative of N′-propylbenzohydrazide with extremely high anti-HCV activity was discovered.
