91817-68-4Relevant articles and documents
Acetonitrile and benzonitrile as versatile amino sources in copper-catalyzed mild electrochemical C-H amidation reactions
Budnikova, Yulia,Kononov, Alexander,Rizvanov, Ildar,Strekalova, Sofia
, p. 37540 - 37543 (2021/12/07)
A mild, efficient electrochemical approach to the site-selective direct C-H amidation of benzene and its derivatives with acetonitrile and benzonitrile has been developed. It has been shown that joint electrochemical oxidation of various arenes in the presence of a copper salt as a catalyst and nitriles leads to the formation of N-phenylacetamide from benzene and N-benzylacetamides from benzyl derivatives (up to 78% yield). A favorable feature of the process is mild conditions (room temperature, ambient pressure, no strong oxidants) that meet the criteria of green chemistry.
SUBSTITUTED TOLYL FUNGICIDE MIXTURES
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Page/Page column 40; 41, (2015/11/03)
Disclosed is a fungicidal composition comprising (a) at least one compound selected from the compounds of Formula 1, N-oxides, and salts thereof, wherein A, Q, R1 and R2 are as defined in the disclosure; and (b) at least one additional fungicidal compound selected from those disclosed herein. Also disclosed is a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of the aforesaid composition.
SUBSTITUTED TOLYL FUNGICIDES
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Page/Page column 29, (2014/05/24)
Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein A, Q, R1 and R2 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.
Magnetic CoFe2O4 nanoparticle immobilized N-propyl diethylenetriamine sulfamic acid as an efficient and recyclable catalyst for the synthesis of amides via the Ritter reaction
Zhao, Xiao-Na,Hu, Hai-Chuan,Zhang, Fu-Jun,Zhang, Zhan-Hui
, p. 258 - 265 (2014/07/08)
A magnetic CoFe2O4 nanoparticle immobilized diamine-N-sulfamic acid (CoFe2O4@SiO2-DASA) was synthesized and used as efficient heterogeneous catalyst for the synthesis of amides via the Ritter reaction under solvent-free conditions. The magnetic nanocatalyst could be readily recovered by applying an external magnet and recycled several times without considerable loss of its catalytic activity.
Benzyl amide-ketoacid inhibitors of HIV-integrase
Walker, Michael A.,Johnson, Timothy,Naidu, B. Narasimhulu,Banville, Jacques,Remillard, Roger,Plamondon, Serge,Martel, Alain,Li, Chen,Torri, Albert,Samanta, Himadri,Lin, Zeyu,Dicker, Ira,Krystal, Mark,Meanwell, Nicholas A.
, p. 4886 - 4890 (2008/02/13)
Integrase is one of three enzymes expressed by HIV and represents a validated target for therapy. Previous reports have demonstrated that the diketoacid-based chemotype is a useful starting point for the design of inhibitors of this enzyme. In this study, one of the ketone groups is replaced by a benzylamide resulting in a new potent chemotype. A preliminary SAR study is carried out to investigate the substitution requirements on the phenyl ring and methylene group of the benzylamide.
Silica gel supported ferric perchlorate: A new and efficient reagent for one pot synthesis of amides from benzylic alcohols
Salehi, Peyman,Motlagh, Aghamorad Rostamian
, p. 671 - 675 (2007/10/03)
Benzylic alcohols react efficiently with nitriles in the presence of silica gel supported ferric perchlorate to produce amides in high yields.
Fe3+-montmorillonite K10: An efficient catalyst for selective amidation of alcohols with nitriles under non-aqueous condition
Lakouraj,Movassagh,Fasihi
, p. 821 - 827 (2007/10/03)
An efficient method for preparation of secondary amides by reaction of alcohols with nitriles is described using a catalytic amount of Fe3+- montmorillonite K10.
Sequence of reactant combination alters the course of the Staudinger reaction of azides with acyl derivatives. Bimanes. 30
Shalev, Deborah E.,Chiacchiera, Stella M.,Radkowsky, Annette E.,Kosower, Edward M.
, p. 1689 - 1701 (2007/10/03)
The Staudinger reaction of azides has now been followed by NMR and other spectroscopic techniques. syn-(Azidomethyl,methyl)(methyl,methyl)(bimane (1) and Ph3P form a triazaphosphadiene intermediate 2 and then the bimane P-triphenyliminophosphorane 3. The iminophosphorane reacts with an acyl chloride to yield an iminophosphonium salt 4 which then forms the oxazaphosphetane 13. The latter undergoes an electrocyclic reversion to form the phosphine oxide and the chloroimines 7E and 7Z, the last being hydrolyzed to the (acylamido)bimane 6. This set of reactions constitutes the "iminophosphorane pathway". A significant diversion of the reaction path to an (N-alkylamino)-phosphonium chloride 8 occurs through reaction of 4 with H2O present in the CDCl3 and through reaction of 3 with HCl. A different azide (α-azido-o-xylene 1b) produces the (acylamido)-o-xylene as the sole product. A less sterically hindered phosphine (tri-2-furylphosphine) reacts more slowly to form the iminophosphorane 3a from the azidobimane 1. Reaction of the bimane P-tri-2-furyliminophosphorane with acyl chloride gives only the (acylamido)bimane 6. If the acyl chloride is mixed with 1, followed by addition of the Ph3P, the triazaphosphadiene adduct 5 is formed via the triazaphosphadiene. The adduct 5 is converted rapidly into a six-membered cyclic compound 11. The latter either loses nitrogen to yield 6 via 7Z and 7E and the phosphine oxide or loses chloride 10 through a novel chloride-induced elimination reaction from its protonated form. The change in procedure thus results in a dramatic change in the reaction pathway, a reaction set that constitutes the "triazaphosphadiene adduet pathway". In the case of α-azido-o-xylene, α-chloro-o-xylene (10b) is the only product. The reactions of the azides 1 or 1b with tri-2-furylphosphine also produce chlorides as the major products accompanied by some acetamido derivatives. The nucleophile-induced reaction explains a "surprising result" (formation of ester rather than amide) reported by Sahlberg et al. (Sahlberg, C.; Jackson, A. M.; Claesson, A. Acta Chem. Scand. 1988, B42, 556-562). The intramolecular "aza-Wittig" reaction may depend on the nucleophilicity of the triazaphosphadiene. A comprehensive mechanistic scheme for the Staudinger reaction of azides is conveniently divided into the following: (A) formation of the triazaphosphadiene (Scheme 1), (B) reactions of the triazaphosphadiene (Scheme 2), and (C) reactions via the iminophosphorane (Scheme 3). Some approximate kinetic parameters are reported for some of the reactions.
Reactions of Thianthrene Cation Radical with Acyclic and Cyclic Alcohols
Shine, Henry J.,Yueh, Wang
, p. 3553 - 3559 (2007/10/02)
Thianthrene cation radical perchlorate (Th(.+)*ClO4(-)) reacted readily with cycloalkanols (C5, C7, C8, and C12), alkan-2-ols (C3, C5, C6, and C8), 3-hexanol, neopentyl alcohol, a number of benzyl alcohols, dl- and (S)-1-phenylethanol, cyclopentyl- and cyclohexylmethanols, the exo- and endo-borneols, and norborneols.Reactions were carried out with an excess of the alcohol in acetonitrile solution containing 2,6-di-tert-butyl-4-methylpyridine.Products were alkenes, ethers, and N-substituted acetamides, depending on the structure of the alcohol.Thianthrene (Th) and its 5-oxide (ThO) were formed in equal amounts.The sum of amounts of products from the alcohol was equal to the amount of ThO.All reactions are interpretable on the basis of the ultimate formation and further reactions of a 5-alkoxythianthreniumyl ion (ROTh(+)).The predominant formation of nortricyclene from the norborneols is striking and is discussed.Swern-Moffatt-type oxidations of the alcohols were not observed.
Simple, high yield preparation of N-benzylacetamides by Lewis acid-catalysed reaction of benzyl chlorides or benzyl methyl ethers with acetonitrile
Kacan,McKillop
, p. 2185 - 2189 (2007/10/02)
Reaction of either benzyl chlorides or benzyl methyl ethers with hydrated ferric chloride in acetonitrile results in smooth Ritter reaction and formation of N-benzylacetamides in excellent yield.
