The isomerization/chlorination of nitrogen heterocyclic O,O-dialkyl thiophosphoramidates with phosphorus oxychloride—A convenient synthesis of nitrogen heterocyclic S-alkyl thiophosphoramidic acid derivatives

✍ Scribed by Chu-Chi Tang; Hui-Fang Lang; Zheng-Jie He

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 286 KB
• Volume: 7
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(199605)7:3<207::aid-hc8>3.0.co;2-6

✦ Synopsis

In this article, it is reported that the isornerization/ chlorination reactions of nitrogen heterocyclic 0, O-dialkyl thiophosphoramidates 5 with equivalent amounts of phosphorus oxychloride give nitrogen heterocyclic S-alkyl thiophosphorochloridates 6 and 0alkyl phosphorodichloridates 3. After removal of the by-products 3 under reduced pressure, the crude products 6 are directly reacted with various nucleophiles, NuH, in the presence of triethyiamine to give nitrogen heterocyclic S-alkyl thiophosphoramidic acid derivatives 7. Thus, a new convenient method has been provided for the synthesis of the title compounds. 0 1996 John Wiley & Sons, Inc.