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Synthesis 2001(11): 1631-1634
DOI: 10.1055/s-2001-16754
PAPER
© Georg Thieme Verlag Stuttgart · New York

Studies on Phosphoroheterocycle Chemistry I: A Facile Synthesis of New Tricyclic Phosphoroheterocycles 1,3,2-Oxazaphospholidino(or Oxazaphosphorino)[3,2-a][1,3,2]benzodiazaphosphorines

Sheng Lou Deng*a, Dong Zhi Liua, Jun Min Huangb, Ru Yu Chenb
a School of Chemical Engineering, Tianjin University, Tianjin 300072, P. R. China
e-Mail: shengloudeng@eyou.com ;
b Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China
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Publication History

Received 19 February 2001
Publication Date:
12 August 2004 (online)

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Abstract

Reaction procedures have been developed for the preparation of structurally different phosphoroheterocyclic compounds. Firstly, the treatment of PCl3 with functionalized compound N-ethyl-2-(β-hydroxyethyl)aminobenzamide gave chlorinated phosphoroheterocycle, 1-(2-chloroethyl)-3-ethyl-2,3-dihydro-1,3,2-benzo-diazaphosphorin-4(1H)-one 2-oxide. Secondly, novel tricyclic phosphoroheterocycles, 1,3,2-oxazaphospholidino(or oxazaphosphorino)[3,2-a][1,3,2]benzodiazaphosphorines, have been conveniently synthesized by cyclization of tris(diethylamino)phosphine with 2-(N-(β or γ-hydroxyalkyl)aminobenzamides. Finally, the reaction of 2-(N-ethoxycarbonylmethyl)amino-N-(2’-hydroxyethyl)-benzamide with P(NEt2)3 afforded five-membered phosphoro-heterocycle, 3-(2’-N-ethoxycarbonylmethylamino)benzoyl-2-diethylamino-1,3,2-oxazaphospholidine-2-sulfide. Additionally, the preliminary bioassays showed that several title compounds possessed herbicidal activity to some extent.

Key words

multifunctional compounds - cyclization - facile synthesis - tricyclic phosphoroheterocycles - herbicidal activity

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The X-ray analyses data are available if necessary.