Synthesis and Structure of O,O‐Diethyl N‐[(trans‐4‐Aryl‐5,5‐dimethyl‐2‐oxido‐2λ⁵‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates

Abstract

A study on the synthesis of the novel N‐(cyclic phosphonate)‐substituted phosphoramidothioates, i.e., O,O‐diethyl N‐[(trans‐4‐aryl‐5,5‐dimethyl‐2‐oxido‐2λ5‐1,3,2‐dioxaphosphorinan‐2‐yl)methyl]phosphoramidothioates 4a–l, from O,O‐diethyl phosphoramidothioate (1), a benzaldehyde or ketone 2, and a 1,3,2‐dioxaphosphorinane 2‐oxide 3 was carried out (Scheme 1 and Table 1). Some of their stereoisomers were isolated, and their structure was established. The presence of acetyl chloride was essential for this reaction and accelerated the process of intramolecular dehydration of intermediate 5 forming the corresponding Schiff base 7 (Scheme 2).

Conformational Analysis of 2-halo-1,3,2-dioxaphosphinanes: A Density Functional Theory (DFT) Investigation

“…The 1,3,2-dioxaphosphorinane derivatives are an interesting group of organophosphorus heterocycles. Various researches focused on evaluating their biological activities, particularly in reference to the design of enzyme inhibitors [1][2][3][4][5][6][7][8]. 1,3,2-dioxaphosphorinanes have attracted a great deal of attention from medicinal and pesticide scientists due to their inclusive stereochemistry and biological activities [9].…”

An eco-friendly procedure for the efficient synthesis of diethyl α-aminophosphonates in aqueous media using natural acids as a catalyst

“…However, one-pot synthesis of α-aminophosphonates remains a favorite due to its versatile route and high-yielding reactions. In the last few decades, intensive synthetic studies were performed in the preparation of α-aminophosphonic acids and their esters [24][25][26][27][28][29]. The Kabachnik-Fields (phospha-Mannich) reaction involving the condensation of primary or secondary amines, oxo compounds (aldehydes and ketones) and >P(O)H species, especially dialkyl phosphites, represents a good choice for the synthesis of α-aminophosphonates that are of significant importance due to their biological activity.…”

Conformation of Sterically Hindered 4-Methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinane in the Solid State and the Solution

“…The 1,3,2-dioxaphosphorinane derivatives, an important class of organophosphorus heterocycles, are interesting compounds because of their biological activities, particularly in reference to the design of enzyme inhibitors [51][52][53][54][55][56][57][58]. As a part of organophosphorus compounds the 1,3,2-dioxaphosphorinanes are also very important in pesticide and medicinal science, owing to their wide biological activities and stereochemistry [59].…”