Synthesis and Bioactivities of Novel 1,3,2-Dioxaphosphorinane 2-one Containing Arylglyoxylonitrile Oxime

Chem. J. Chinese Universities ›› 1999, Vol. 20 ›› Issue (10): 1574.

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Synthesis and Bioactivities of Novel 1,3,2-Dioxaphosphorinane 2-one Containing Arylglyoxylonitrile Oxime

MA Zhi-Hua, SHAO Rui-Lian, MA Hong-Min, CHENG Jun-Ran, HUANG Run-Qiu

Institute of Elemento Organic Chemistry, State Key Laboratory of Elemento Organic Chemistry, Nankai University, Tianjin 300071, China

Received:1999-02-07 Online:1999-10-24 Published:1999-10-24

Abstract

Abstract: The reaction of trans-2-chloro-2-oxo-4-phenyl-5,5-dimethyl-1,3,2-dioxapho-sphorinane(Ⅱ) with arylglyoxylonitrile oximes in the presence of PTC resulted in diastereomers of novel cyclic phosphate of arylglyoxylonitrile oxime(Ⅲ). The configuration and ratio of cis/trans diastereomers of Ⅲ were confined by ¹HNMR, ³¹PNMR and X-ray diffraction analysis. The reaction of arylaldoxime with trans-Ⅱ yielded an unstable arylaldoxime cyclic phosphate which was decomposed through Beckmann fragmentation to give nitrile and cyclic phosphate acid. The bioassay indicated that compound cis-Ⅲd showed a high antiviral activity against TMV.

Key words: 1,3,2-Dioxaphosphorinane, Arylglyoxylonitrile oximes, Diastereomers, An-tiphytoviral activity

CLC Number:

O623

TrendMD:

MA Zhi-Hua, SHAO Rui-Lian, MA Hong-Min, CHENG Jun-Ran, HUANG Run-Qiu . Synthesis and Bioactivities of Novel 1,3,2-Dioxaphosphorinane 2-one Containing Arylglyoxylonitrile Oxime[J]. Chem. J. Chinese Universities, 1999, 20(10): 1574.

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Synthesis and Bioactivities of Novel 1,3,2-Dioxaphosphorinane 2-one Containing Arylglyoxylonitrile Oxime

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