98977-53-8Relevant academic research and scientific papers
Application of naftifine analogue in control of agricultural plant diseases
-
Paragraph 0011-0016; 0057-0060, (2020/07/21)
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
C-N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis
Nazari, S. Hadi,Tiempos-Flores, Norma,Forson, Kelton G.,Bourdeau, Jefferson E.,Michaelis, David J.
, p. 10646 - 10654 (2018/09/06)
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.
Combining Copper-Catalyzed Hydroboration with Palladium-Catalyzed Suzuki Coupling for the One-pot Synthesis of Arylallylamines under Micellar Conditions
Horn, Pedro A.,Braun, Roger K.,Isoppo, Victória G.,Costa, Jessie S. da,Lüdtke, Diogo S.,Moro, Angélica V.
, p. 2322 - 2328 (2017/07/07)
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.).
Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides
West, Thomas H.,Spoehrle, Stéphanie S.M.,Smith, Andrew D.
, p. 4138 - 4149 (2017/06/29)
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
Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water
Da Costa, Jessie S.,Braun, Roger K.,Horn, Pedro A.,Lüdtke, Diogo S.,Moro, Angélica V.
, p. 59935 - 59938 (2016/07/11)
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
Stereoselective synthesis of (E)-3,3-diaryl and (E)-3-aryl-3-aryloxy allylamines and allylalcohols from trans-cinnamyl chloride and alcohol
Limberger, Jones,Claudino, Thiago S.,Monteiro, Adriano L.
, p. 45558 - 45565 (2015/02/19)
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.
Deammoniative condensation of primary allylic amines with nonallylic amines
Wang, Yong,Li, Manbo,Ma, Xiantao,Liu, Congrong,Gu, Yonghong,Tian, Shi-Kai
, p. 741 - 751 (2014/10/15)
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
Stereoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with grignard reagents. Synthesis of naftifine
Shakhmaev,Sunagatullina,Zorin
, p. 322 - 331 (2014/06/09)
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.
N-heterocyclic carbene C,S palladium(II) π-allyl complexes: Synthesis, characterization, and catalytic application in allylic amination reactions
Krishnan, Deepa,Wu, Meiyi,Chiang, Minyi,Li, Yongxin,Leung, Pak-Hing,Pullarkat, Sumod A.
supporting information, p. 2389 - 2397 (2013/06/27)
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
Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines
Utsunomiya, Masaru,Miyamoto, Yoshiki,Lpposhi, Junji,Ohshima, Takashi,Mashima, Kazushi
, p. 3371 - 3374 (2008/02/12)
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.
