- Application of naftifine analogue in control of agricultural plant diseases
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The invention discloses application of any compound of naftifine analogues H-01 to H-22 in control of agricultural plant fungal diseases. Biological activity tests indicate that the derivatives show certain inhibitory activity on the six plant diseases, i
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Paragraph 0011-0016; 0057-0060
(2020/07/21)
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- C-N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis
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Amination of allylic alcohols is facilitated via cooperative catalysis. Catalytic Ti(O-i-Pr)4 is shown to dramatically increase the rate of nickel-catalyzed allylic amination, and mechanistic experiments confirm activation of the allylic alcohol by titanium. Aminations of primary and secondary allylic alcohols are demonstrated with a variety of amine nucleophiles. Diene-containing substrates also cyclize onto the nickel allyl intermediate prior to amination, generating carbocyclic amine products. This tandem process is only achieved under our cooperative catalytic system.
- Nazari, S. Hadi,Tiempos-Flores, Norma,Forson, Kelton G.,Bourdeau, Jefferson E.,Michaelis, David J.
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p. 10646 - 10654
(2018/09/06)
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- Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides
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The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement pr
- West, Thomas H.,Spoehrle, Stéphanie S.M.,Smith, Andrew D.
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p. 4138 - 4149
(2017/06/29)
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- Combining Copper-Catalyzed Hydroboration with Palladium-Catalyzed Suzuki Coupling for the One-pot Synthesis of Arylallylamines under Micellar Conditions
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Herein we report the one-pot dual-metal catalytic synthesis of arylallylamines, by combination of a Cu-catalyzed hydroboration with a Pd-catalyzed Suzuki arylation, using a broad range of aryl halides. Importantly, the reaction sequence was entirely performed in water, in the presence of small amounts of SPGS-550M, without the need of solvent switch or addition of organic co-solvents, rendering it operationally simple and environmentally benign. The usefulness of this methodology was highlighted in a short synthesis of the pharmaceutically important compound naftifine. (Figure presented.).
- Horn, Pedro A.,Braun, Roger K.,Isoppo, Victória G.,Costa, Jessie S. da,Lüdtke, Diogo S.,Moro, Angélica V.
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p. 2322 - 2328
(2017/07/07)
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- Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water
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The Cu-catalyzed hydroboration of alkynes in operationally simple and environmentally friendly conditions is reported. The reactions are performed in water, at room temperature, under micellar catalysis. Conditions to form the α or β borylated products se
- Da Costa, Jessie S.,Braun, Roger K.,Horn, Pedro A.,Lüdtke, Diogo S.,Moro, Angélica V.
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p. 59935 - 59938
(2016/07/11)
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- Stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols from trans-cinnamyl chloride and alcohol
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In this work we describe the regio and stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols. The starting materials are the non-expensive commercially available cinnamyl alcohol and chloride. The bromination/dehydrobromination sequence furnished the (E)-3-bromo-3-phenylallyl amines and alcohol as single regioisomers and with high stereoselectivity (>98%). These vinyl bromides were used as substrates in cross-coupling reactions furnishing the arylated products with good to excellent yields and total E-configuration retention. With this protocol, we were able to produce regio and stereospecifically trisubstituted olefins and vinyl ethers by Suzuki cross-coupling and Ullmann vinylation.
- Limberger, Jones,Claudino, Thiago S.,Monteiro, Adriano L.
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p. 45558 - 45565
(2015/02/19)
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- Deammoniative condensation of primary allylic amines with nonallylic amines
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An unprecedented deammoniative condensation reaction of primary allylic amines with nonallylic amines has been developed through C-N bond cleavage. In the presence of 5 mol% palladium diacetate, 10 mol% 1,4-bis(diphenylphosphino) butane (dppb), and 5 mol% p-toluenesulfonic acid (TsOH), a range of α-unbranched primary allylic amines smoothly underwent deammoniative condensation with nonallylic amines in an α-selective fashion to give structurally diverse secondary and tertiary amines in good to excellent yields and E selectivity. Replacing dppb with racemic 2,2-bis(diphenylphosphino)-1,1- binaphthyl (BINAP) permitted the deammoniative condensation of enantioenriched α-chiral primary allylic amines with nonallylic amines to proceed with complete retention of configuration. Electrospray ionization (ESI) mass spectrometric analysis of the reaction mixture permitted the identification of some π-allylpalladium intermediates, and plausible mechanisms have been proposed to account for the regioselectivity and stereospecificity of the deammoniative condensation reaction. A range of enantioenriched primary allylic amines underwent palladium/acid-catalyzed direct substitution with nonallylic amines in a stereospecific manner. Copyright
- Wang, Yong,Li, Manbo,Ma, Xiantao,Liu, Congrong,Gu, Yonghong,Tian, Shi-Kai
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p. 741 - 751
(2014/10/15)
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- Stereoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with grignard reagents. Synthesis of naftifine
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A general procedure for the synthesis of trans- and cis-allylamines has been developed on the basis of iron-catalyzed cross-coupling of Grignard reagents with stereochemically pure 3-chloroprop-2-en-1-amines prepared by allylation of amines with commercially available 1,3-dichloropropene isomers.
- Shakhmaev,Sunagatullina,Zorin
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p. 322 - 331
(2014/06/09)
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- N-heterocyclic carbene C,S palladium(II) π-allyl complexes: Synthesis, characterization, and catalytic application in allylic amination reactions
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A series of five-membered N-heterocyclic carbene C,S palladium(II) π-allyl complexes were successfully developed and characterized. Structural analyses of these complexes revealed that the organopalladium chelates adopt a skew-envelope conformation with a
- Krishnan, Deepa,Wu, Meiyi,Chiang, Minyi,Li, Yongxin,Leung, Pak-Hing,Pullarkat, Sumod A.
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supporting information
p. 2389 - 2397
(2013/06/27)
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- Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines
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A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.
- Utsunomiya, Masaru,Miyamoto, Yoshiki,Lpposhi, Junji,Ohshima, Takashi,Mashima, Kazushi
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p. 3371 - 3374
(2008/02/12)
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- Palladium(0)-Catalyzed Substitution of Allylic Substrates in an Aqueous-Organic Medium
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A palladium(0)-water soluble catalyst prepared in situ from palladium acetate and the sulfonated triphenyl phosphine P(C6H4-m-SO3Na)3 (or tppts) is an efficient catalyst for allylic substitution with various carbon and heteronucleophiles in an aqueous-organic medium, allowing a very easy separation of the product(s) and the recycling of the catalyst.
- Blart, Errol,Genet, Jean Pierre,Safi, Mohamed,Savignac, Monique,Sinou, Denis
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p. 505 - 514
(2007/10/02)
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- THE BORONIC ACID MANNICH REACTION: A NEW METHOD FOR THE SYNTHESIS OF GEOMETRICALLY PURE ALLYLAMINES
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Reaction of vinyl boronic acids with the adducts of secondary amines and paraformaldehyde gives tertiary allylamines with the same geometry.This simple and practical method was used for the synthesis of geometrically pure naftifine, a potent antifungal agent.
- Petasis, Nicos A.,Akritopoulou, Irini
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p. 583 - 586
(2007/10/02)
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- Synthesis and Structure-Activity Relationships of Naftifine-Related Allylamine Antimycotics
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Naftifine (1) is the first representative of the new antifungal allylamine derivatives.Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals.A tertiary allylamine function seems to be a prerequisite for activity against fungi.By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations.Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.
- Stuetz, Anton,Georgopoulos, Apostolos,Granitzer, Waltraud,Petranyi, Gabor,Berney, Daniel
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p. 112 - 125
(2007/10/02)
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