Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones.
1-Hydroxy-3,5-dimethyl-2,4-benzodioates (4-hydroxyisophthalates) were prepared by [3+3] cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 3-ethoxycarbonyl-4-trimethylsilyloxy-3-penten-2-one which is synthesized from (symmetrical) ethyl 2-acetylacetoacetate. The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy-2-alkoxycarbonyl-2-en-1-ones, readily available by reaction of beta-ketoesters with trialkyl orthoformiates, provide a convenient and regioselective approach to a great variety of 3-substituted 1-hydroxy-2,4-benzodioates that are not readily available by other methods.
Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059, Rostock, Germany.
Mohanad
M
Shkoor
Abdolmajid
A
Riahi
Olumide
O
Fatunsin
Ibrar
I
Hussain
Mirza A
MA
Yawer
Mathias
M
Lubbe
Stefanie
S
Reim
Helmut
H
Reinke
Christine
C
Fischer
Peter
P
Langer
D000438:Alcohols / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D001643:Bridged Bicyclo Compounds; D002070:Butadienes; D012821:Silanes; C059688:alkoxyl radical