Highly convergent one-pot four-component regioselective synthesis of 4H-benzo [f]chromenes via annulation of beta-oxodithioesters

作者：Samai Subhasis; Nandi Ganesh Chandra; Singh Maya Shankar^*

来源：Tetrahedron, 2012, 68(4): 1247-1252.

DOI：10.1016/j.tet.2011.11.051

• Four-component reaction
• Indium trichloride (InCl3)
• Benzo[f]chromene
• beta-Oxodithioesters
• Transesterification

Highly efficient regioselective protocol for the synthesis of hitherto unreported 4H-benzo[f]chromenes has been developed by one-pot four-component coupling of aromatic aldehydes, beta-naphthol, beta-oxodithioesters, and primary alcohols in the presence of InCl3. This transformation presumably proceeds via domino Knoevenagel condensation/Michael addition/intramolecular cyclodehydration/transesterification sequence creating four new bonds and one stereocenter in a single operation. Further, alcohol plays dual role as a reactant as well as reaction medium.

• 出版日期2012-1-28