Domino processes as a tool for recovering substandard reactions. Synthesis and use of nitroacetic acid esters and amides

Org Lett. 2002 Mar 21;4(6):965-8. doi: 10.1021/ol0255357.

Abstract

[reaction: see text] Elusive nitroacetic acid esters and amides were obtained through a halogen exchange reaction of the corresponding bromoacetic acid derivatives with polymer-supported nitrite anion. The process is flawed by a side product catalyzed degradation of the products. Domino processes turned out to be a powerful tool for overcoming such drawbacks, converting a substandard reaction into an efficient multicomponent preparation of 4-hydroxy-4,5-dihydroisoxazoles.