Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

Yamada, Kohei; Kamimura, Naoto; Kunishima, Munetaka

doi:10.3762/bjoc.13.146

Cited by 12 publications

(11 citation statements)

References 37 publications

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“…Results and Discussion: Chemistry A number of methods have been applied for preparing di-and trisubstituted oxazoles. They may be classified into three general types, including cyclisation (Davidson oxazole synthesis and Robinson-Gabriel method), functionalization and multi-component methods (Yamada et al, 2017). In all these cases, however, the reactions require strong acidic conditions and / or high temperature.…”

Section: Materials and Methods: Chemistrymentioning

confidence: 99%

Computer Prediction and Synthesis of New Oxazoles Based on an 8-Thiosubstituted 1,3,7-Trimethylxanthine Skeleton

Zlatkov

Mitkov

Georgieva

2018

CBUP

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The synthesis of new oxazole derivatives was carried out under Davidson synthesis conditions from O-acylacyloins with an 8-thiosubstituted 1,3,7-trimethylxanthine skeleton and ammonium acetate in a 1:10 ratio in glacial acetic acid media. The starting O-acylacyloins were obtained as products from the interaction of the sodium salt of 2-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylthio)acetic acid and a-haloketones. The structures of the new compounds were proven by microanalyses and spectral data. The PASS online web application was used to predict the biological activity spectra of the obtained derivatives and to determine the most promising biological effects for further experimental testing. Thus, it has been shown that the synthesized compounds are a promising class for the creation of substances with a wide range of biological activity. The substrate/metabolite specificity of the tested compounds was also predicted using SMP web-service. The studied compounds were considered to perform most probably with CYP2 substrate activity.

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Section: Materials and Methods: Chemistrymentioning

confidence: 99%

Computer Prediction and Synthesis of New Oxazoles Based on an 8-Thiosubstituted 1,3,7-Trimethylxanthine Skeleton

Zlatkov

Mitkov

Georgieva

2018

CBUP

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“…Several protocols for regioselective C−H activation have been developed, [19,20,26,27] but typically were applied to structurally simple oxazoles stabilized by a C2‐(hetero)aryl group. Alternatively, transition metal‐mediated cross‐couplings of 5‐bromooxazoles [27–29] and oxazolyl‐5‐ethers [30] have been realized, but often suffer from limited substrate scope as well as modest stability of the oxazole ring such activated. (Hetero)aryl esters, [31] carbonates, [32] carbamates, [32,33] sulfonates, [34] and sulfamates [32,33,35] have been explored as C−O electrophiles in selected cross‐couplings.…”

Section: Figurementioning

confidence: 99%

Effective C5‐Arylation of Peptide‐Integrated Oxazoles: Almazole D

Oberheide

Arndt

2020

Adv Synth Catal

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An efficient functionalization approach of oxazoles by using Pd‐catalyzed cross‐coupling reactions is reported. Oxazolone formation and subsequent sulfamoylation in situ are facilitated by employing N,N‐diethylsulfamoyl imidazolium triflate. Cross‐couplings provide both oxazole‐arenes and oxazole‐heteroarenes and were compatible with sensitive and epimerization‐prone substrates, as exemplified by the total synthesis of the natural product almazole D.

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“…[19] Driven by important applications of oxazole derivatives, various synthetic methodologies for their synthesis have been developed. The classical approaches to the synthesis of trisubstituted oxazoles include dehydrative cyclization of acyclic precursors described in numerous reviews; [1][2][3] newer methods rely on Ni-catalyzed Suzuki-Miyaura coupling, [21] cross-coupling reactions of 2-, 4-and 5-bromooxazoles, [22] and palladiumcatalyzed CÀ H activation. [23] Notably, direct approaches to highly functionalized oxazoles are rare, thus making a general and efficient procedure to access trisubstituted oxazoles -in particular, those containing both amino and carboxyl groupshighly desirable.…”

Section: Introductionmentioning

confidence: 99%

Functionalized 5‐Amino‐4‐cyanoxazoles, their Hetero‐ and Macrocyclic Derivatives: Preparation and Synthetic Applications

et al. 2021

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An approach to a series of new 5-amino-4-cyanoxazoles is described. Synthesis of the title compounds relied on a twostep sequence including heterocyclization of 2-amido-3,3dichloroacrylonitriles with aliphatic secondary amines (dimethylamine, morpholine), primary aliphatic amines with active functional groups (2-aminoethanol and glycine ethyl ester), and aniline. An efficient and straightforward protocol introduces a carboxylate group at the C-2 position of 5-amino-4-cyanoxazoles, connected to the heterocycle directly or through an aliphatic linker. This carboxylic group is an attractive motif that can be found in a variety of drug-relevant compounds and also used for further modifications. Furthermore, efficient transformations of selected trisubstituted compounds were used to demonstrate their rich synthetic potential -e. g., as precursors to 2-(4-cyano-5-(dimethylamino)oxazol-2-yl)acetamides, oxazole-containing macrocyclic structures, 2-(oxazol-2-yl) acetamides, amino pyrazoles, 3-(4-cyano-5-aminoxazol-2-yl) coumarins, and oxazole amino acids.[a] D.

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Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

Cited by 12 publications

References 37 publications

Computer Prediction and Synthesis of New Oxazoles Based on an 8-Thiosubstituted 1,3,7-Trimethylxanthine Skeleton

Computer Prediction and Synthesis of New Oxazoles Based on an 8-Thiosubstituted 1,3,7-Trimethylxanthine Skeleton

Effective C5‐Arylation of Peptide‐Integrated Oxazoles: Almazole D

Functionalized 5‐Amino‐4‐cyanoxazoles, their Hetero‐ and Macrocyclic Derivatives: Preparation and Synthetic Applications

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