TY - JOUR
T1 - Friedel-crafts reaction of activated benzene rings with captodative and electron-deficient alkenes. A one-step synthesis of the natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate
AU - Aguilar, Raúl
AU - Benavides, Adriana
AU - Tamariz, Joaquín
PY - 2004
Y1 - 2004
N2 - Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1-acetylvinyl-1-p-nitrobenzoate (9), and with the electron-deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a-8c. We also describe a one-step synthesis of the antifungal and larvicidal natural product methyl 3-(2,4,5-trimethoxyphenyl) propionate (6), by reaction of 1,2,4-trimethoxybenzene with 8a under microwave irradiation.
AB - Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1-acetylvinyl-1-p-nitrobenzoate (9), and with the electron-deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a-8c. We also describe a one-step synthesis of the antifungal and larvicidal natural product methyl 3-(2,4,5-trimethoxyphenyl) propionate (6), by reaction of 1,2,4-trimethoxybenzene with 8a under microwave irradiation.
KW - Captodative olefins
KW - Friedel-Crafts
KW - Methyl 3-(2,4,5-trimethoxyphenyl) propionate
UR - http://www.scopus.com/inward/record.url?scp=4444282581&partnerID=8YFLogxK
U2 - 10.1081/SCC-200026193
DO - 10.1081/SCC-200026193
M3 - Artículo
SN - 0039-7911
VL - 34
SP - 2719
EP - 2735
JO - Synthetic Communications
JF - Synthetic Communications
IS - 15
ER -