Beilstein J. Org. Chem.2022,18, 889–915, doi:10.3762/bjoc.18.90
synthesis of 1,2-azaphospholidine and 1,2-azaphospholine 2-oxides/sulfides and their fused derivatives.
Keywords: azaphospholidine; azaphospholine; phosphonolactam; γ-phosphonolactam; phosphinolactam; γ-phosphinolactam; γ-phostam; Introduction
Phosphaheterocycles are a class of important organic compounds
1,2-azaphospholidine 2-oxide (γ-phosphonolactam) from N,N’-diphenyl 3-chloropropylphosphondiamide (1), which was cyclized to 1-phenyl-2-phenylamino-γ-phosphonolactam (2) in the presence of NaOH in methanol via the C–N bond formation (Scheme 1) [21].
In 1974, the strategy was applied for the synthesis
of 2-ethoxy-1-methyl-γ-phosphonolactam (6) for potential insecticides. Diethyl 3-bromopropylphosphonate (3) was first monochlorinated with phosphorus pentachloride in carbon tetrachloride followed by aminolysis with methylamine, affording ethyl N-methyl-(3-bromopropyl)phosphonamidate (5). Compound 5
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Graphical Abstract
Figure 1:
Biologically active 1,2-azaphospholine 2-oxide derivatives.