TY - JOUR
T1 - A facile synthetic route to 1,1-disubstituted 2,3-dihydro-1H-benz[f]indene-4,9-diones
AU - Pal, S.
AU - Banik, B. K.
AU - Ghatak, U. R.
PY - 1992
Y1 - 1992
N2 - A facile synthetic route is described for 1,1-dimethyl and 1-methoxycarbonyl-1-methyl substituted 2,3-dihydro-1H-benz[f]indene-4,9-diones 7a, 7c and 7d from the corresponding 1,2,3,4-tetrahydrofluorenes 2a, 2c, and 2d involving ruthenium-catalyzed periodate oxidation of the tetrasubstituted double bond to the respective 6,7,8,9,10,11-hexahydro-5,10-dioxo-5H-benzocyclononenes 3a, 3c and 3d, cyclization-dehydration (aromatization) and methylation to 2,3-dihydro-4-methoxy-1H-benz[f]indenes 6a, 6c and 6d, followed by oxidation with pyridinium chlorochromate/Celite. The only exception to this trend is 2b, which on ruthenium-catalyzed periodate oxidation directly affords 7b.
AB - A facile synthetic route is described for 1,1-dimethyl and 1-methoxycarbonyl-1-methyl substituted 2,3-dihydro-1H-benz[f]indene-4,9-diones 7a, 7c and 7d from the corresponding 1,2,3,4-tetrahydrofluorenes 2a, 2c, and 2d involving ruthenium-catalyzed periodate oxidation of the tetrasubstituted double bond to the respective 6,7,8,9,10,11-hexahydro-5,10-dioxo-5H-benzocyclononenes 3a, 3c and 3d, cyclization-dehydration (aromatization) and methylation to 2,3-dihydro-4-methoxy-1H-benz[f]indenes 6a, 6c and 6d, followed by oxidation with pyridinium chlorochromate/Celite. The only exception to this trend is 2b, which on ruthenium-catalyzed periodate oxidation directly affords 7b.
UR - http://www.scopus.com/inward/record.url?scp=0026482136&partnerID=8YFLogxK
U2 - 10.1055/s-1992-26304
DO - 10.1055/s-1992-26304
M3 - Artículo
SN - 0039-7881
SP - 1073
EP - 1075
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 11
ER -