New Efficient and Flexible Synthesis of Polysubstituted Pyrroles

Article abstract of DOI:10.1016/0040-4039(95)01717-V

The Lewis acid mediated reaction of readily available 2-acetoxypropanal-N,N-dimethylhydrazone 1 with various open chain and cyclic silyl enol ethers 2 leads directly or via 4-oxoaldehyde-N,N-dimethylhydrazones 3 to N-(dimethylamino)-pyrroles 4.The subsequent reductive N-N bond cleavage provides an efficient and flexible method for the preparation of alkyl-aryl-di- and trisubstituted pyrroles 5.