42718-19-4Relevant academic research and scientific papers
Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition
Teegardin, Kip A.,Gotcher, Lacey,Weaver, Jimmie D.
supporting information, p. 7239 - 7244 (2018/11/25)
The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.
Ru-catalyzed C[sbnd]H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
Ruiz, Sara,Sayago, Francisco J.,Cativiela, Carlos,Urriolabeitia, Esteban P.
, p. 407 - 418 (2016/12/16)
The reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl2]2 (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond activation step is assisted by carboxylates, and N-fluoro-2,4,6-trimethylpyridinium triflate works as the terminal oxidant. The process shows a remarkable tolerance to the presence of diverse electron-releasing and electron-attracting functional groups at the phenyl ring of the amino acid. In addition, the reaction of phenylglycine derivatives (1a–1f) with methyl acrylate (4a) catalyzed by [Ru(cymene)Cl2]2 (10%) under the same experimental conditions, gives the corresponding 3,N-disubstituted isoindoline-1-carboxylates 5 through C[sbnd]H/N[sbnd]H coupling. Isoindolines 5 are obtained as a mixture of diastereoisomers, with moderate to high values of diastereomeric excess (up to 80%).
Efficient C2 functionalisation of 2H-2-imidazolines
Bon, Robin S.,Sprenkels, Nanda E.,Koningstein, Manoe M.,Schmitz, Rob F.,De Kanter, Frans J. J.,Doemling, Alexander,Groen, Marinus B.,Orru, Romano V. A.
, p. 130 - 137 (2008/09/20)
Alkylation and oxidation of 2H-2-imidazolines, followed by regioselective deprotection, thionation and microwave-assisted Liebeskind-Srogl reaction, efficiently led to 2-aryl-2-imidazolines as new analogues of p53-hdm2 interaction inhibitors (Nutlins). Th
GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
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Page/Page column 31, (2008/12/07)
Compounds of Formula (I) or a salt thereof are provided: wherein R6, R7, R8, R9, X, Ar, n, and m are as defined in the description. Uses of the compounds as medicaments, and in the manufacture of medicament for
GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
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Page/Page column 29, (2008/12/07)
Compounds of formula (I) or a salt thereof are provided: wherein R6, R7, R9, R10, R11, X, n, p, Ar and m are as defined in the description. Uses of the compounds as medicaments, and in the manufacture
GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
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Page/Page column 30, (2008/12/07)
Compounds of formula (I) or a salt thereof are provided wherein R1, R2, R3, R4, R5, R6, R7, R9, R10, X, n, p and m are as defined in the description. Uses o
GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
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Page/Page column 33, (2008/12/07)
Compounds of formula (I) or a salt thereof are provided wherein R1, R2, R6, R7, R8, R9 and m are as defined in the description. Uses of the compounds as medicaments, and in the manufacture
Glyt1 Transporter Inhibitors and Uses Thereof in Treatment of Neurological and Neuropsychiatric Disorders
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Page/Page column 25, (2008/12/08)
The invention provides a compound of formula (I) or a solvate thereof: wherein R1, R2, R3, R4, R5, R6, and n are as defined in the specification, and uses of such compounds. The compounds i
N-PHENYL-2-0X0-1,4-DIAZASPIR0 [4.5] DEC-3-EN-1-YL ACETAMIDE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORTER INHIBITORS
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Page/Page column 33, (2008/06/13)
Compounds of formula (I) and salts and solvates are provided: Formula (I) Uses of the compounds as medicaments, and in the manufacture of medicament for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention d
1-(2-ARYL-2-OXOETHYL)-3-PHENYL-1, 4-DIAZASPIRO [4.5]DEC-3-EN-2-ONE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORTER INHIBITORS
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Page/Page column 31-32, (2008/06/13)
Novel acetophenone compounds of formula (I), compositions containing (I), processes for the preparation of (I), and use of (I) as inhibitors of the glycine transporter, are provided. Definitions of Ar, R5, R6, R7, R8
