TY - JOUR
T1 - Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones
AU - Cruz, María Del Carmen
AU - Jiménez, Fabiola
AU - Delgado, Francisco
AU - Tamariz, Joaquín
PY - 2006/3/17
Y1 - 2006/3/17
N2 - A new approach is described for the synthesis of substituted indoles 5, through an intramolecular and regioselective Friedel-Crafts cyclization of enaminones 6a-h catalyzed by Lewis acids. Compounds 6 were prepared from the 2-anilinocarbonyl compounds 7, by treatment with DMFDMA under thermal or microwave (MW) irradiation conditions. An alternative and shorter one-pot two-step synthesis of indoles 5 was achieved starting from compounds 7 and promoted by MW radiation, including the elusive 2-acetylindoles 5i-m.
AB - A new approach is described for the synthesis of substituted indoles 5, through an intramolecular and regioselective Friedel-Crafts cyclization of enaminones 6a-h catalyzed by Lewis acids. Compounds 6 were prepared from the 2-anilinocarbonyl compounds 7, by treatment with DMFDMA under thermal or microwave (MW) irradiation conditions. An alternative and shorter one-pot two-step synthesis of indoles 5 was achieved starting from compounds 7 and promoted by MW radiation, including the elusive 2-acetylindoles 5i-m.
KW - Enaminones
KW - Friedel-Crafts annulations
KW - Indoles
KW - Lewis acid catalysis
KW - Microwaves
UR - http://www.scopus.com/inward/record.url?scp=33645403649&partnerID=8YFLogxK
U2 - 10.1055/s-2006-933135
DO - 10.1055/s-2006-933135
M3 - Artículo
SN - 0936-5214
SP - 749
EP - 755
JO - Synlett
JF - Synlett
IS - 5
ER -