Scope and Limitations of a Novel Synthesis of 3-Arylazonicotinates

Abstract

The reaction of 3-oxo-3-phenyl-2-phenylhydrazonal with functionally substituted and heteroaromatic substituted acetonitrile to yield arylazonicotinic acid derivatives and 5-arylsubstituted pyridines was established. In some cases the produced nicotinates could not be isolated as they underwent thermally induced 6π-electrocyclization yielding polynuclear pyridine derivatives.

Keywords

• 3-oxo-3-phenyl-2-phenylhydrazonal
• arylazonicotinic acid
• pyridine
• electrocyclization
• heteroaromatics