TY - JOUR
T1 - An efficient method for the synthesis of 2′,3′-nonsubstituted cycloalkane-1,3-dione-2-spirocyclopropanes using (2-bromoethyl)-diphenylsulfonium trifluoromethanesulfonate
AU - Nambu, Hisanori
AU - Ono, Naoki
AU - Hirota, Wataru
AU - Fukumoto, Masahiro
AU - Yakura, Takayuki
N1 - Publisher Copyright:
© 2016 The Pharmaceutical Society of Japan.
PY - 2016
Y1 - 2016
N2 - An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.
AB - An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.
KW - 1,3-cyclohexanedione
KW - Cyclopropane
KW - Double alkylation
KW - Spiro compound
KW - Sulfonium salt
UR - http://www.scopus.com/inward/record.url?scp=85000789213&partnerID=8YFLogxK
U2 - 10.1248/cpb.c16-00625
DO - 10.1248/cpb.c16-00625
M3 - 学術論文
C2 - 27904084
AN - SCOPUS:85000789213
SN - 0009-2363
VL - 64
SP - 1763
EP - 1768
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 12
ER -