Details
| Original language | English |
|---|---|
| Pages (from-to) | 6109-6112 |
| Number of pages | 4 |
| Journal | TETRAHEDRON |
| Volume | 59 |
| Issue number | 32 |
| Publication status | Published - 15 Jul 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.
Keywords
- Condensation, Intermediate substrate, Pyrazine
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: TETRAHEDRON, Vol. 59, No. 32, 15.07.2003, p. 6109-6112.
Research output: Contribution to journal › Article › Research › peer review
}
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.
PY - 2003/7/15
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
UR - http://www.scopus.com/inward/record.url?scp=0041845348&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(03)00948-7
DO - 10.1016/S0040-4020(03)00948-7
M3 - Article
AN - SCOPUS:0041845348
VL - 59
SP - 6109
EP - 6112
JO - TETRAHEDRON
JF - TETRAHEDRON
SN - 0040-4020
IS - 32
ER -