Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine

Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review

Autorschaft

  • Toshinari H. Kurniadi
  • Rachid Bel Rhlid
  • Marcel A. Juillerat
  • Thierry Gefflaut
  • Jean Bolte
  • Ralf G. Berger

Organisationseinheiten

Externe Organisationen

  • Nestlé SA
  • Université Blaise-Pascal
Forschungs-netzwerk anzeigen

Details

OriginalspracheEnglisch
Seiten (von - bis)6109-6112
Seitenumfang4
FachzeitschriftTETRAHEDRON
Jahrgang59
Ausgabenummer32
PublikationsstatusVeröffentlicht - 15 Juli 2003

Abstract

The aroma compounds 2-ethenyl-3,5-dimethylpyrazine 1 and 3-ethenyl-2,5-dimethylpyrazine 2 were synthesized via a new chemical route. The key steps of the synthesis involve cyclocondenzation of 1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione and 1,2-propanediamine, aromatization of the resulting 5,6-dihydropyrazines, and subsequent Retro-Diels-Alder reaction to generate pyrazines 1 and 2. Pyrazine 1, a powerful odorant, was obtained in large excess (8:2) when endo-1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione was used as intermediate substrate.

ASJC Scopus Sachgebiete

Zitieren

Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine. / Kurniadi, Toshinari H.; Rhlid, Rachid Bel; Juillerat, Marcel A. et al.
in: TETRAHEDRON, Jahrgang 59, Nr. 32, 15.07.2003, S. 6109-6112.

Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review

Kurniadi, TH, Rhlid, RB, Juillerat, MA, Gefflaut, T, Bolte, J & Berger, RG 2003, 'Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine', TETRAHEDRON, Jg. 59, Nr. 32, S. 6109-6112. https://doi.org/10.1016/S0040-4020(03)00948-7
Kurniadi, T. H., Rhlid, R. B., Juillerat, M. A., Gefflaut, T., Bolte, J., & Berger, R. G. (2003). Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine. TETRAHEDRON, 59(32), 6109-6112. https://doi.org/10.1016/S0040-4020(03)00948-7
Kurniadi TH, Rhlid RB, Juillerat MA, Gefflaut T, Bolte J, Berger RG. Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine. TETRAHEDRON. 2003 Jul 15;59(32):6109-6112. doi: 10.1016/S0040-4020(03)00948-7
Kurniadi, Toshinari H. ; Rhlid, Rachid Bel ; Juillerat, Marcel A. et al. / Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine. in: TETRAHEDRON. 2003 ; Jahrgang 59, Nr. 32. S. 6109-6112.
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title = "Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine",
abstract = "The aroma compounds 2-ethenyl-3,5-dimethylpyrazine 1 and 3-ethenyl-2,5-dimethylpyrazine 2 were synthesized via a new chemical route. The key steps of the synthesis involve cyclocondenzation of 1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione and 1,2-propanediamine, aromatization of the resulting 5,6-dihydropyrazines, and subsequent Retro-Diels-Alder reaction to generate pyrazines 1 and 2. Pyrazine 1, a powerful odorant, was obtained in large excess (8:2) when endo-1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione was used as intermediate substrate.",
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TY - JOUR

T1 - Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine

AU - Kurniadi, Toshinari H.

AU - Rhlid, Rachid Bel

AU - Juillerat, Marcel A.

AU - Gefflaut, Thierry

AU - Bolte, Jean

AU - Berger, Ralf G.

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Y1 - 2003/7/15

N2 - The aroma compounds 2-ethenyl-3,5-dimethylpyrazine 1 and 3-ethenyl-2,5-dimethylpyrazine 2 were synthesized via a new chemical route. The key steps of the synthesis involve cyclocondenzation of 1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione and 1,2-propanediamine, aromatization of the resulting 5,6-dihydropyrazines, and subsequent Retro-Diels-Alder reaction to generate pyrazines 1 and 2. Pyrazine 1, a powerful odorant, was obtained in large excess (8:2) when endo-1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione was used as intermediate substrate.

AB - The aroma compounds 2-ethenyl-3,5-dimethylpyrazine 1 and 3-ethenyl-2,5-dimethylpyrazine 2 were synthesized via a new chemical route. The key steps of the synthesis involve cyclocondenzation of 1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione and 1,2-propanediamine, aromatization of the resulting 5,6-dihydropyrazines, and subsequent Retro-Diels-Alder reaction to generate pyrazines 1 and 2. Pyrazine 1, a powerful odorant, was obtained in large excess (8:2) when endo-1-[bicyclo[2.2.1]5-hepten-2-yl]-1,2-propanedione was used as intermediate substrate.

KW - Condensation

KW - Intermediate substrate

KW - Pyrazine

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