5-Hydroxyindoles by intramolecular alkynol-furan diels-alder cycloaddition.

ABSTRACT: A convergent approach provides a convenient access to synthetically and biologically useful 3,4-disubstituted 5-hydroxyindoles. The one-pot procedure uses microwave heating to initiate an intramolecular [4 + 2]-cycloaddition of an alkynol segment onto a furan followed by a fragmentation, aromatization, and N-Boc deprotection cascade. Yields range from 15 to 74%, with aromatic substituents providing better conversions. 4-Trimethylsilylated analogues undergo a 1,3-silatropic rearrangement to give the O-TMS ethers.

SUBMITTER: LaPorte M 

PROVIDER: S-EPMC3684082 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature