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A-Arylglycine

The standard synthesis of sydnones (Section 5.03.9.2) has benefited from the use of A,./V,iV, iV -tetrabromobenzene-1,3-disulfonamide (TBBDS) as an efficient promoter of the one-pot conversion of various iV-arylglycines to sydnone products <2006H(68)2343>. Conversion of A-arylglycines to sydnones was achieved in 85 to 95% yield using a combination of NaN02 and AczO in CH2C12 promoted by TBBDS, under mild and neutral conditions. [Pg.236]

Since the early review on sydnones by Stewart (192) and the subsequent coverage by Potts (1), several new applications of these remarkably stable mesoionic heterocycles have been described. In particular, the synthesis of pyrazoles from sydnones has been pursued by several groups. Badachikar et al. (193) prepared several new potential antibacterials (297) from the appropriate sydnones 296, which were synthesized in the standard fashion by the cyclodehydration of the corresponding A-nitroso-A-arylglycine. [Pg.735]

The Pd-catalyzed amidocarbonylation was used for the synthesis of a-arylglycines that are antimicrobial agents and enzyme inhibitors.Thus, iV-acyl-a-arylglycines and other iV-acyl-a-amino acids were synthesized in highly efficient and economical manner under the standard conditions. In a similar manner, an advanced intermediate for the synthesis of antiepileptic Levetiracetam 7, iV-acetyl-a-aminobutyric acid 6, was synthesized in high yield from propanal and acetamide (Equation (1)). ... [Pg.513]

Several reports have employed a more traditional approach where the use of enantio-pure chiral amino auxiliaries, that, after the successful Strecker reaction, can be chemically modified to yield the free amino acids. For example, Chakraborty and co-workers have reported the highly diastereoselective addition of trimethylsilyl cyanide to a variety of a-phenylglycinol-derived benzaldimines [16]. (S)-a-Methylbenzylamine has been used as a chiral auxiliary for the asymmetric Strecker reaction [17]. (R)-Phenylglycinol has been utilized as a chiral auxiliary from the asymmetric Strecker reaction products of aldehydes in the synthesis of a,a-disubstituted amino acids [18]. (R)- and (S)-2-Amino-2-phenylethanol were used as chiral auxiliaries in the synthesis of optically pure a-arylglycines [19]. [Pg.192]

Other reports for the boron-Mannich reaction include the synthesis of aminophenol derivatives,561 a-arylglycines,576 a growth hormone secretagogue NN703,577 a polyhydroxyindolizine alkaloid uniflorine A,578 and cyclic ct-amino acids.579 The reaction has been applied to solution-phase reactions580 and the solid-phase reaction581-585 for the synthesis of libraries of peptides, a-amino acids, and bicyclic diketopiperazines. The reactions were accelerated by the irradiation of microwave.586... [Pg.192]

Cyclization of the anilide 213 using TiCU produced the 3-chloro-substituted oxindole 214 (Equation 69), whereas a similar reaction induced by BF3-OEt2 gave the corresponding methoxy-substituted derivative <1998T4889>. Lewis acids have also been used in an approach to indole-2-carboxylates based on cyclization of (Z)-A(A -dimethyl-aminopropenoates derived by exposure of A -arylglycinates to DMEDMA <2006SL749>. [Pg.295]

Petasis, N. A., Goodman, A., Zavialov, I. A. A new synthesis of a-arylglycines from aryl boronic acids. Tetrahedron 1997, 53,16463-16470. [Pg.650]

IT c h lpiperidine-l-oxyl (TEMPO) jl.ohols with NaOCl affords the tt r without disturbing extant jr-fcr to the carboxylic acid stage cn.iiitiopure a-arylglycines from... [Pg.351]

Eor pioneering examples, see (a) N. A. Petasis, I. Akritopoulou, Tetrahedron Lett. 1993, 34, 583-586. The boronic acid Mannich reaction a new method for the synthesis of geomet-ricaUy pure aUylamines. (b) N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1997, 119, 445-446. A new and practical synthesis of a-amino acids from alkenyl boronic acids, (c) N. A. Petasis, A. Goodman, I. A. Zavialov, Tetrahedron 1997, 53, 16463-16470. A new synthesis of a-arylglycines from aryl horonic acids. [Pg.146]

For some selected examples, see (a) Y. Perez-Fuertes, J. E. Taylor, D. A. TickeU, M. F. Mahon, S. D. Bull, T. D. James, J. Org. Chem. 2011, 76, 6038-6047. Asymmetric Strecker synthesis of a-arylglycines. (b) J. R. Donald, R. R. Wood, S. F. Martin, ACS Comb. Sci. 2012,14,135-143. Application of a sequential multicomponent assembly process/Huisgen cycloaddition strategy to the preparation of libraries of 1,2,3-triazole-fused 1,4-benzodiazepines, (c) L. Y. V. Mendez, V.V. Kouznetsov, Curr. Org. Chem. 2013, 10, 969-973. First girgensohnine analogs prepared through InClj-catalyzed Strecker reaction and their bioprospection. [Pg.357]

Scheme 6.40 The use of the Petasis-Akritopoulou reaction for the synthesis of a-arylglycines from aryl... Scheme 6.40 The use of the Petasis-Akritopoulou reaction for the synthesis of a-arylglycines from aryl...
The synthesis of A/-acyl-a-chloroglycine and its use in the preparation of other a-substituted glycines has been described.N-Acylhemiaminals, prepared from glyoxylic acid and amides, carbamates, or ureas, can be converted into N-acyl-a-arylglycines by reaction with aromatic hydrocarbons in sulphuric acid. The same type of hemiaminals may be converted into N-acyl-y-keto-a-amino-acids by reactions with 1,3-dicarbonyl compounds again in the presence of concentrated sulphuric acid. °°... [Pg.124]


See other pages where A-Arylglycine is mentioned: [Pg.167]    [Pg.231]    [Pg.218]    [Pg.415]    [Pg.212]    [Pg.573]    [Pg.673]    [Pg.17]    [Pg.350]    [Pg.251]    [Pg.226]    [Pg.26]    [Pg.140]    [Pg.251]    [Pg.317]    [Pg.58]    [Pg.415]   
See also in sourсe #XX -- [ Pg.170 , Pg.226 ]




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Arylglycine

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