Synthesis of 5-isonitroso-1,3-dioxane-4,6-dione (2: isonitroso Meldrum's acid) and related compounds and their reactions were described. Compound (2) reacted with various alcohols to give hydroxyiminoacetic acid esters in moderate yields. Compound 2 was acetylated in the usual manner to give 5-acetoxyimino-1,3-dioxane-4,6-dione (9) as a stable crystalline substance, which acted not as a heterodiene but as a heterodienophile and underwent hetero Diels-Alder reaction with various dienes to form [4 + 2] adducts.
- 6-dione hydroxyiminoacetic acid Diels-Alder reaction asymmetric reaction 2-azabicy-clo[2.2.1]hept-5-ene carbocyclic nucleoside
ASJC Scopus subject areas
- Drug Discovery