Synthesis of heteroaryl substituted α‐amino acid derivatives, polyols, and related compounds

Svete, Jurij

doi:10.1002/jhet.5570390302

Cited by 47 publications

(54 citation statements)

References 45 publications

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“…2 For example, they were employed in the 'ring switching' preparation of 3-heteroarylalanine-, 3 3-heteroarylalaninol-, 4 10 In continuation of our research in the field of chiral 3-(dimethylamino)propenoate analogues, we report the preparation and transformations of benzyl (3S,4E)-4-[(dimethylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamate 5, a novel representative in this series, and its utilisation in the solution phase parallel synthesis of benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates 7c-n.…”

Section: Introductionmentioning

confidence: 99%

Parallel solution phase synthesis of benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates

Pirc¹,

Bevk²,

Grdadolnik³

et al. 2003

Arkivoc

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Benzyl (3S,4E)-4-[(dimethylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamate 5 was prepared in 4 steps from L-aspartic acid 1. Acid-catalysed treatment of 5 with amines 6 gave the dimethylamine substitution products 7. Benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates 7c-n were prepared by parallel solution phase synthesis from 5 and anilines 6c-n in 45-94% yields. Enaminone 5 reacted with potassium cyanide in the presence of 18-crown-6 to afford benzyl 4-cyanomethyl-5-oxo-2,5-dihydrofuran-3-ylcarbamate 9. Upon reaction of 9 with nitrile oxide 10 the 1,2,4-oxadiazole derivative 11 was isolated in poor yield, while treatment of 9 with diazomethane 12 furnished the methylation products 13 and 14.

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Section: Introductionmentioning

confidence: 99%

Parallel solution phase synthesis of benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates

Pirc¹,

Bevk²,

Grdadolnik³

et al. 2003

Arkivoc

Self Cite

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“…Enaminones are polyfunctional compounds possessing both electrophilic and nucleophilic properties. Typical electrophilic positions are C-3 (the dimethylaminomethylene center) and C-1 (the carbonyl carbon center) with the reactivity order C-3 > C-1 while a typical nucleophilic position is C-2 (48)(49)(50)(51) . The regioselectivity of the 3+2 cycloaddition reaction of compound 2 is in accordance with this hypothesis and excludes the formation of other products.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of New Pyrazolones and Fused Pyrazole Derivatives as Antimicrobial Agents

2010

Egypt. J. Chem.

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“…It is also well known that the magnitudes of the coupling constant ( 3 J CH ) between nuclei with cis configuration around the C=C double bond are smaller (2-6 Hz) than those of trans-oriented nuclei (8)(9)(10)(11)(12). [62,64] The magnitudes of couplings 3 J C(1)ÀH(2') = 7 Hz (trans) and 3 J C(3)ÀH(2') = 5 Hz (cis) confirms the E configuration around the exocyclic C=C double bond. [64] Use of short-and long-range 15 C/ 15 N correlation in the lysine side chain in ubiquitin.…”

Section: Conformational and Configurational Analysismentioning

confidence: 99%

Measurement and Applications of Long‐Range Heteronuclear Scalar Couplings: Recent Experimental and Theoretical Developments

2012

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The use of long-range heteronuclear couplings, in association with (1)H-(1)H scalar couplings and NOE restraints, has acquired growing importance for the determination of the relative stereochemistry, and structural and conformational information of organic and biological molecules. However, the routine use of such couplings is hindered by the inherent difficulties in their measurement. Prior to the advancement in experimental techniques, both long-range homo- and heteronuclear scalar couplings were not easily accessible, especially for very large molecules. The development of a large number of multidimensional NMR experimental methodologies has alleviated the complications associated with the measurement of couplings of smaller strengths. Subsequent application of these methods and the utilization of determined J-couplings for structure calculations have revolutionized this area of research. Problems in organic, inorganic and biophysical chemistry have also been solved by utilizing the short- and long-range heteronuclear couplings. In this minireview, we discuss the advantages and limitations of a number of experimental techniques reported in recent times for the measurement of long-range heteronuclear couplings and a few selected applications of such couplings. This includes the study of medium- to larger-sized molecules in a variety of applications, especially in the study of hydrogen bonding in biological systems. The utilization of these couplings in conjunction with theoretical calculations to arrive at conclusions on the hyperconjugation, configurational analysis and the effect of the electronegativity of the substituents is also discussed.

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Synthesis of heteroaryl substituted α‐amino acid derivatives, polyols, and related compounds

Cited by 47 publications

References 45 publications

Parallel solution phase synthesis of benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates

Parallel solution phase synthesis of benzyl (3S,4E)-4-[(arylamino)methylidene]-5-oxotetrahydrofuran-3-ylcarbamates

Synthesis of New Pyrazolones and Fused Pyrazole Derivatives as Antimicrobial Agents

Measurement and Applications of Long‐Range Heteronuclear Scalar Couplings: Recent Experimental and Theoretical Developments

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