Toward understanding the scope of Baylis-Hillman reaction: Synthesis of 3-(2- hydroxyphenyl)indolin-2-ones and polycyclic fused furans

Abstract

A facile one-pot synthesis of 3-(2-hydroxyphenyl)indolin-2-ones has been developed via the TiCl4-me- diated Baylis-Hillman (B-H) reaction of N-substituted isatins and cyclohex-2-enone, followed by treatment of the in situ generated B-H alcohols with aq HBr. Baylis-Hillman reaction of aromatic cyclic 1, 2-diones with cycloalk-2-enones under the influence of TiCl4 has been successfully performed and the resulting Baylis-Hillman adducts have been conveniently transformed into pentacyclic and hexacyclic fused furan derivatives. © 2010 Elsevier Ltd. All rights reserved.