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

被引:8
作者
Miao, Zhiwei [1 ]
Zhang, Jianfeng [1 ]
Cui, Zhanwei [1 ]
Wang, Bin [1 ]
Chen, Ruyu [1 ]
机构
[1] Nankai Univ, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
D O I
10.1002/hlca.200790201
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 lambda(5)-1,3,2-dioxaphosphorinan-2-yl)methyl]phosphoramidothioates 4a-1. 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).
引用
收藏
页码:1932 / 1939
页数:8
相关论文
共 50 条
[21]   N,N-′bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphinan-2-yl)ethane-1,2-diamine [J].
Li, Hai-Bing ;
Li, Ya ;
Xiong, De-Jun ;
Tian, De-Mei .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 :O606-O607
[22]   SYNTHESIS AND CRYSTAL-STRUCTURE OF OPTICALLY-ACTIVE 2-[BENZYL(PHENYL)AMINO]ETHYL 5-(5,5-DIMETHYL-2-OXO-1,3,2-DIOXAPHOSPHORINAN-2-YL)-1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3-PYRIDINECARBOXYLATE (NZ-105) [J].
SAKODA, R ;
MATSUMOTO, H ;
SETO, K .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (09) :2377-2381
[23]   Studies on the synthesis and biological activities of 2-[(2-chloro-5-pyridylmethylamino)(aryl)methyl]-4-aryl-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxides [J].
Sun, Feng-Mei ;
Shi, De-Qing .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (10) :1398-1402
[24]   Acetyl chloride-mediated synthesis of trans-2-[(diethoxyphosphorylamino)alkyl]-4-aryl-5,5-dimethyl-1,3,2λ5-dioxaphosphorinane-2-oxide [J].
Miao, Zhiwei ;
Zhang, Jianfeng ;
Cui, Zhanwei ;
Chen, Ruyu .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (05) :630-635
[25]   N-(10-bromoanthracen-9-ylmethyl)-n-[2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzyl]methylamine at 240 K [J].
Barkhuizen, DA ;
Howie, RA ;
Maguire, GEM ;
Rademeyer, M .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 :O571-O573
[26]   Synthesis and antimicrobial activity of N-(substituted)-N'-(2,3-dihydro2-oxido-5-benzoyl-1H-1,3,2-benzodiazaphosphol-2-yl) ureas [J].
Reddy, PVG ;
Reddy, CS ;
Raju, CN .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (07) :860-863
[27]   O,O-diethyl ({1-[(6-chloropyridin-3-yl)methyl]5-methyl-1H-1,2,3-triazol-4-ylcarbonyloxy}-phenylmethyl)phosphonate [J].
Chen, Xiao-Bao ;
Shi, De-Qing .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :O172-O174
[28]   LIPASE-CATALYZED ENANTIOSYNTHESIS OF (R)- AND (S)-2-[BENZYL(PHENYL)AMINO]ETHYL 5-(5,5-DIMETHYL-2-OXO-1,3,2-DIOXAPHOSPHORINAN-2-YL)-1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3-PYRIDINECARBOXYLATE (NZ 105) [J].
EBIIKE, H ;
YAMAZAKI, Y ;
ACHIWA, K .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (07) :1251-1253
[29]   AN X-RAY STUDY OF N6-(2-THIO-4-METHYL-1,3,2-DIOXAPHOSPHORINAN-2-YL)-3-BETA-PHENYLISOPROPYLSYDNONIMINE, C15H20N3D3PS [J].
BORISOV, EV ;
NEVSKII, NN ;
AKHLEBININ, AK ;
NIFANTEV, EE .
JOURNAL OF STRUCTURAL CHEMISTRY, 1985, 26 (01) :144-146
[30]   Synthesis of N-[aryl(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl] thioacetamide derivatives [J].
Zhiani, Rahele .
JOURNAL OF CHEMICAL RESEARCH, 2016, (01) :26-28