Water extract of red mud: an efficient and renewable medium for environmentally benign synthesis of 2-amino-4H-chromenes

Abstract

In this study, an efficient and convenient domino Michael addition/intramolecular cyclization protocol is presented for the synthesis of biologically relevant 2-amino-4H-chromenes in short reaction times using water extract of red mud (WERM) at room temperature. Red mud is generated abundantly as wastes in aluminum industries and this is the first report to utilize WERM as an effective and renewable medium in organic synthesis. As the precursor material is a waste, the present method is environmentally benign and economical. The final 2-amino-4H-chromenes were obtained in high yields by simple precipitation and subsequent washing by aqueous ethanol which eliminates the chromatographic separation. The present method is tolerated by electronically diverse functional groups and also applicable for large-scale synthesis. Moreover, WERM was recovered from the reaction medium and reused for several cycles without significant loss of reactivity.

Keywords: 2-Amino-4H-chromene; Cyclization; Michael addition; Red mud; Sustainable chemistry; WERM.