A Novel Route to Spiro Phosphorus-Heterocycle via Lawesson's Reagent

Abstract

2-Aryl-spiro-[5,5]-1,3,2-dioxaphosphorinane-2-sufides were prepared by the cyclization reaction of Lawesson's reagent with pentaerythritol and monobenzalpentaerythritol, respectively.

6-Bromo-3-(4-chlorophenyl)-2-(4-methoxyphenyl)-3,4-dihydro-1,3,2-benzoxazaphosphinine 2-sulfide

“…An increasing interest has been shown for the past 20 years in the chemistry of phosphorus heterocycles owing to their unique physicochemical properties (He et al, 2002) and potential biological activities (Rao et al, 2000). Many classes of phosphorus heterocyclic system bearing PO and PN units, such as cyclophosphamide and its derivatives, are antitumor agents (Gilard et al, 1999).…”

Applications of Lawesson’s Reagent in Organic and Organometallic Syntheses

“…Reagents and Conditions: a) 1.2 equiv LR, toluene, reflux, 1 h, 31% He et al described another route for the preparation of spiroheterocycles (Scheme 52). Treatment of pentaerythitol 134 (2.2 equiv) with LR (1 equiv) in anhydrous MeCN at reflux led to the corresponding spiro-compound dioxaphorphorinane 135 184.…”

Synthesis and Antioxidant Properties of New Substituted 8‐Methyl‐6‐phenyl‐5,6‐dihydro‐4H‐1,3,2‐benzodioxaphosphocine‐2‐oxide Derivatives

“…Focused on the chemistry of organophosphorus heterocyclics, attention has been increased from past three decades because of their unique physicochemical properties [9] and potential biological activities [10][11][12][13]. Majority of organophosphorus heterocyclic systems include structural moieties with P-O and P-N bonds like cyclophosphamide, and its derivatives as proven antitumor agents are the earliest examples [14].…”