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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

✍ Scribed by Zhiwei Miao; Jianfeng Zhang; Zhanwei Cui; Bin Wang; Ruyu Chen

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
210 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

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‐2__λ__^5^‐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).

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✍ P. Vasu Govardhana Reddy; Y. Hari Babu; C. Suresh Reddy 📂 Article 📅 2003 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 27 KB

## Abstract __N__‐(Substituted aryl/cyclohexyl)‐__N'__‐[5‐bromo‐5‐nitro‐2‐oxido‐1,3,2‐dioxaphosphorinane‐2‐yl]ureas RR'P(O)NHC(O)NHR' (__5__) were synthesized by the reactions of 2‐bromo‐2‐nitro‐1,3‐propanediol **(4)** with chlorides of aryl/cyclohexyl carbamidophosphoric acids **(3)** in the prese