- Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles
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NH-1,2,3-Triazoles undergo a ring cleavage in reactions with fluorinated acid anhydrides (trifluoroacetic, difluoroacetic, chlorodifluoroacetic, and pentafluoropropionic anhydrides) by nitrogen acylation and acid-mediated triazole ring opening. Structurally diverse fluoroalkylated oxazoles were prepared from 4,5-disubstituted-1,2,3-triazoles. Efficient synthesis of 2-acylaminoketones was achieved from 4-substituted 1,2,3-triazoles. Finally, easy access to fluoroalkylated imidazoles and 1,2,4-triazines was developed by a one-pot two-step route from NH-triazoles, fluorinated anhydrides, and amines or hydrazine.
- Motornov, Vladimir,Beier, Petr
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supporting information
p. 1958 - 1963
(2022/03/27)
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- Self-Catalyzed Rapid Synthesis of N-Acylated/ N-Formylated α-Aminoketones and N-Hydroxymethylated Formamides from 3-Aryl-2 H-Azirines and 2-Me/Ph-3-Aryl-2 H-Azirines
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A rapid and effective method has been established for the synthesis of N-acylated α-aminoketone derivatives by the reaction of 3-aryl-2H-azirines and highly substituted 2-Me/Ph-3-aryl-2H-azirines with various carboxylic acids under ambient air within 10 min at room temperature. N-Trifluoroacetylated α-aminoketones with different substituents have been reported in the presence of trifluoroacetic acid. This protocol is equally effective to synthesize N-formylated α-aminoketone and N-hydroxymethylated formamide derivatives.
- De, Aramita,Majee, Adinath,Santra, Sougata,Zyryanov, Grigory V.
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supporting information
p. 3926 - 3930
(2020/07/14)
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- Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts
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N-Aminopyridinium salts generate nitrogen-centered radicals by means of photoredox catalysis. Herein, we report that they can be trapped by enol equivalents to give α-amino carbonyl compounds in excellent yields. The broad synthetic utility of this method is demonstrated by functionalization of ketones, aldehydes, esters enol equivalents, vinyl ethers, and 1,3-diketones without the need for prior conversion to enol derivatives. The developed method is easily scalable, offers broad substrate scope, high chemoselectivity.
- Goliszewska, Katarzyna,Rybicka-Jasińska, Katarzyna,Szurmak, Jakub,Gryko, Dorota
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p. 15834 - 15844
(2019/11/03)
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- Photoactivated N-Acyliminoiodinanes Applied to Amination: an ortho-Methoxymethyl Group Stabilizes Reactive Precursors
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N-Acyliminoiodinanes were characterized for the first time by X-ray structural analysis. The ortho-methoxymethyl group and the carbonyl oxygen coordinate to the iodine atom of the iminoiodinane. Activation of the N-acyliminoiodinane was achieved by photoirradiation at 370 nm, thereby enabling reaction with various silyl enol ethers to give α-aminoketone derivatives in good to high yield. N-sulfonyliminoiodinanes bearing ortho substituents were used in photoinduced amination.
- Kobayashi, Yusuke,Masakado, Sota,Takemoto, Yoshiji
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supporting information
p. 693 - 697
(2018/01/17)
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- Synthesis of chiral TFA-protected α-amino aryl-ketone derivatives with friedel-crafts acylation of α-amino acid n-hydroxysuccinimide ester
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Chiral N-protected α-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel-Crafts acylation of N-protected α-amino acids. One of the drawbacks of this reaction
- Tachrim, Zetryana Puteri,Oida, Kazuhiro,Ikemoto, Haruka,Ohashi, Fumina,Kurokawa, Natsumi,Hayashi, Kento,Shikanai, Mami,Sakihama, Yasuko,Hashidoko, Yasuyuki,Hashimoto, Makoto
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- M-STAGE KINESIN INHIBITOR
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A mitotic kinesin Eg5 inhibitor which comprises a thiadiazoline derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient: [wherein R1 represents a hydrogen atom and the like, R2 represents a hydrogen atom, -C(=W)R6 (wherein W represents an oxygen atom or a sulfur atom, and R6 represents substituted or unsubstituted lower alkyl and the like) and the like, R3 represents -C(=Z)R19 (wherein Z represents an oxygen atom or a sulfur atom, and R19 represents substituted or unsubstituted lower alkyl and the like) and the like, R4 represents substituted or unsubstituted lower alkyl and the like, and R5 represents substituted or unsubstituted aryl and the like] and the like are provided.
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Page/Page column 82
(2010/11/08)
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- THIADIAZOLINE DERIVATIVE
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(wherein R1 and R4 are the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkynyl, substituted or unsubstituted lower alkenyl, or the like; R5 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like; R2 represents -C(-W)R6 or the like; R3 represents a hydrogen atom, -C(=WA)R6A, or the like) Antitumor agents which comprises a thiadiazoline derivative represented by the aforementioned general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient are provided.
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- Nitrido ruthenium porphyrins: Synthesis, characterization, and amination reactions with hydrocarbon or silyl enol ethers
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An unprecedented synthetic strategy was used for the preparation of nitrido ruthenium(VI) porphyrins such as 1. The structure of 1 features a Ru-N (nitrido) distance of 1.656(5) A. Reactions of nitrido ruthenium(VI) porphyrins with silyl enol ethers or indan, in the presence of trifluoroacetic anhydride, afforded N-trifluoroacetyl amines in up to 84% yield.
- Leung, Sarana Ka-Yan,Huang, Jie-Sheng,Liang, Jiang-Lin,Che, Chi-Ming,Zhou, Zhong-Yuan
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p. 340 - 343
(2007/10/03)
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- Baker's Yeast Reduction of α-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols
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Enzymatic reduction of α-acylaminoacetophenones with fermenting baker's yeast afforded optically active (R)-2-acylamino-1-arylethanols.Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.
- Izumi, Taeko,Fukaya, Katsumi
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p. 1216 - 1221
(2007/10/02)
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- Friedel-Crafts Acylation with N-(Trifluoroacetyl)-α-amino Acid Chlorides. Application to the Preparation of β-Arylalkylamines and 3-Substituted 1,2,3,4-Tetrahydroisoquinolines
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Several N-(trifluoroacetyl)-α-amino acid chlorides have been reacted with benzene, anisole, and veratrole in the presence of AlCl3 or SnCl4 to produce the corresponding aromatic ketones in fair to high yields.The products are reductible under neutral or acidic conditions to the corresponding N-(trifluoroacetyl)-β-hydroxy-β-arylakylamines or N-(trifluoroacetyl)-β-arylalkylamines.The latter can be readily detrifluoroacetylated by mild basic hydrolysis and thence converted to the corresponding 3-substituted 1,2,3,4-tetrahydroisoquinolines by condensation with formaldehyde.
- Nordlander, Eric J.,Payne, Mark J.,Njoroge, George F.,Balk, Michael A.,Laikos George D.,Vishwanath, Vasanth M.
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p. 4107 - 4111
(2007/10/02)
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