7563-05-5Relevant academic research and scientific papers
BEMP-promoted C(4)-alkylation of 4-alkyloxazol-5(4 H)-ones: A rapid and efficient route to α,α-dialkyl-α-amino acids
Lee, Yeon-Ju,Seo, Jeyoung,Kim, Dong-Guk,Park, Hyeung-Geun,Jeong, Byeong-Seon
, p. 701 - 704 (2013/05/09)
Rapid and efficient C(4)-alkylation of 4-alkyloxazol-5(4H)-ones has been achieved by the utilization of BEMP as base. 4,4-Dialkyloxazol-5(4H)-ones, which can easily be hydrolyzed into free α,α-dialkyl-α-amino acids, were obtained in high yields (up to 99%
DAST-mediated cyclization of α,α-disubstituted-α- acylaminoketones: Efficient and divergent synthesis of unprecedented heterocycles
Bigot, Aurelien,Blythe, Judith,Pandya, Chirag,Wagner, Trixie,Loiseleur, Olivier
supporting information; experimental part, p. 192 - 195 (2011/03/20)
The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substit
Solid-phase de novo synthesis of a (±)-2-deoxy-glycoside
Lucchesi, Céline,Arboré, Amélie,Pascual, Sagrario,Fontaine, Laurent,Maignan, Christian,Dujardin, Gilles
experimental part, p. 844 - 849 (2010/06/21)
The solid-phase synthesis of methyl 2-deoxy-3-O-benzyl-d,l-arabino-hexopyranoside was achieved in a six-step sequence via a de novo strategy based on the hetero-Diels-Alder reaction of a vinyl ether supported on an azalactone-functionalized polystyrene re
NOVEL MICROBIOCIDES
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Page/Page column 31-32, (2009/12/02)
Compounds of formula (I), in which the substituents are as defined in claim 1, are suitable for use as microbiocides.
SYNTHESIS OF α-SUBSTITUTED α-AMINO ACIDS BY THE ALKYLATION OF 5-OXAZOLINONE DERIVATIVES
Slavinskaya, V. A.,Sile, D. E.,Katkevich, M. Yu.,Korchagova, E. Kh.,Lukevits, E.
, p. 724 - 728 (2007/10/02)
Methods have been developed for the alkylation of 5-oxazolinone derivatives in DMF in the presence of K2CO3, KOH, or diisopropylethylamine and a phase transfer catalyst as well as for the preparation of α-methylphenylalanine, α-methylalanine, α-methylalanine, and the methyl ester of N-benzoyl-α-methylalanine.Increasing the initial concentration of the starting 5-oxazolinone in the reaction mixture leads to a sharp drop in the yield of reaction products due to side condensation reactions.The reaction of 2-phenyl-4-benzyl-5-oxazolinonewith ethyl iodide gave a dimer, mamely, 3-(benzoylamino)-3,5-dibenzylpyrrolidine-2,4-dione.
3-(Dimethylamino)-2,2-dimethyl-2H-azirine as an Aib Equivalent; Synthesis of Aib Oligopeptides
Obrecht, Daniel,Heimgartner, Heinz
, p. 102 - 115 (2007/10/02)
3-(Dimethylamino)-2,2-dimethyl-2H-azirine (1) reacts with carboxylic acids at 0-25 degC to give 2-acylamino-N,N,2-trimethylpropionamides (=2-acylamino-N,N-dimethylisobutyramide, acyl-Aib-NMe2) in excellent yields (Scheme 2 and 3).Examples of α-amino-, α-h
Synthesis of 4,4-Disubstituted 1,3-Thiazol-5(4H)-thiones
Jenny, Christjohannes,Heimgartner, Heinz
, p. 374 - 388 (2007/10/02)
An easy synthesis for the 1,3-thiazol-5(4H)-thiones 5, a class of heterocycles which have hitherto only been available with difficulty, is described.Reaction of 3-amino-2H-azirines 25 with thiocarboxylic acids at 0 deg yields monothiodiamides of type 20 (Scheme 6) which, on treatment with Lawesson reagent at 100 deg, undergo thiation and cyclization to give 5 in good yield.
REACTIONS OF 2-PHENYL-4,4-DIMETHYL-2-OXAZOLIN-5-ONE AND 2-PHENYL-4-ETHYL-2-OXAZOLIN-5-ONE with KO2 IN APROTIC SOLVENTS
Chuaqui, Claudio A.,Delaney, Sabine,Merritt, John
, p. 2947 - 2951 (2007/10/02)
The reactions of 2-phenyl-4,4-dimethyl-2-oxazolin-5-one (I) and 2-phenyl-4-ethyl-2-oxazolin-5-one (II) with KO2 in tetrahydrofuran and freon are studied.Superoxide reacts with I to yield the N-benzoyl-α-aminoacid ring-opening product, indicating that O2 produces a nucleophilic attack at the carbonyl group of the oxazolinone.The oxazolinone II yields, in addition to the N-benzoyl-α-amino derivative, N-propanoyl benzamide (III) as the main reaction product.The results strongly suggest that III is formed after O2 has abstracted a proton from II, and then, species resulting from secondary reactions, such as oxygen, attack II to yield the final products.Several mechanistic pathways are discussed.
