Heterocycles through Domino Reactions with Trimethyl Aconitate, a Versatile Synthetic Building Block

Abstract

The multitalented synthetic reagent trimethyl aconitate (1) is a renewable raw material with a high density of functional groups that up to now has only been scarcely used as a C₆ building block. Domino reactions with 1 consisting of imine additions and intramolecular acylations provide simple access to heteropolycycles in one-pot reactions. For example, 1 reacts with N-methylbenzylidenamine (2) to give the spiro[pyrrolidinone-3,3'-dihydropyrrolinone] 3 in 40 % yield.

Keywords: acylation; domino reactions; imines; nitrogen heterocycles; spiro compounds.