One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based on regioselective [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes.
6-(Thien-2-yl) and 6-(fur-2-yl)salicylates are prepared by TiCl(4)-mediated [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-(thien-2-yl)- and 3-(fur-2-yl)-3-silyloxy-2-en-1-ones, respectively. The regioselectivity of the cyclization depends on the substitution pattern of the 3-silyloxy-2-en-1-one.
Hussain
Ibrar
I
Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Riahi
Abdolmajid
A
Yawer
Mirza Arfan
MA
Villinger
Alexander
A
Fischer
Christine
C
Görls
Helmar
H
Langer
Peter
P
D002070:Butadienes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D012459:Salicylates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D002070:Butadienes; D012459:Salicylates