Synthesis of dibenzo[b,d]pyran-6-ones based on [3 + 3] cyclizations of 1,3-bis(silyl enol ethers) with 3-silyloxy-2-en-1-ones.
Functionalized dibenzo[b,d]pyran-6-ones were prepared by formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 3-silyloxy-2-en-1-ones or 1,1-diacetylcyclopropane to give functionalized salicylates, Suzuki cross-coupling reactions of the corresponding triflates, and subsequent BBr3-mediated lactonization. A second approach to dibenzo[b,d]pyran-6-ones relies on the [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 1-(2-methoxyphenyl)-1-(trimethylsilyloxy)alk-1-en-3-ones and subsequent BBr3-mediated lactonization.
Hussain
Ibrar
I
Institut für Chemie, Universität Rostock, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany.
Nguyen
Van Thi Hong
VT
Yawer
Mirza Arfan
MA
Dang
Tuan Thanh
TT
Fischer
Christine
C
Reinke
Helmut
H
Langer
Peter
P
D001565:Benzoates / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D004987:Ethers / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D012459:Salicylates / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*
D001565:Benzoates; D004987:Ethers; D011714:Pyrans; D012459:Salicylates; D012821:Silanes; D010100:Oxygen