Phosphorylacetic Acid Thioamides As Key Substances for Phosphorylated Heterocycles

Abstract

Diethoxyphosphorylthioacetamide in a reaction with 2,3-dichloroquinoxaline acted as a thionating reagent, giving diethoxyphosphorylacetonitrile and 2-chloro-3-[(3-chloro-2-quinoxalinyl)-thio]quinoxaline. Base-catalyzed reactions of phosphorythioacetamides with N-methylquinoxalinium iodide proceeded stereoselectively to yield cis-3-phosphoryl-1,3,3a,4,9,9a-hexahydro-2H-pynola[2,3-b]quinoxaline-2-thiones.

Keywords:

• 1,3,3a,4,9,9a-hexahydro-2H-pyrrolo[2,3-b]quinoxaline-2-thiones
• 2,3-dichloroquinoxaline
• annulation
• N-methylquinoxalinium iodide
• phosphorythioacetamides