Formation of Benzooxaphosphole Oxide Heterocyclic System by the Ring-Contractive Arbuzov-Michaelis Isomerization of Alkoxy-Substituted Benzodioxaphosphorins

Abstract

A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. Some synthetic possibilities of the new reaction disclosed here are demonstrated by introducing a pharmacophoric 5-O-nucleoside to th P(IV) atom leading to the 3H-benzo[d][1,2]oxaphosphole 2-oxide system by this new rearrangement reaction.

Keywords:

• 2-hydroxybenzylic Alcohol
• Arbuzov-Michaelis-type Isomerization
• Benzodioxaphosphorins
• Benzooxaphosphole Oxides
• Cyclosaligenyl Nucleotides
• Saligenin