Synthesis of Alkyl (5-Oxo-2-thioxo-[1,3,4]thiadiazinan-6-ylidene)acetates by the Reaction of N-Aminorhodanine, Dialkyl Acetylenedicarboxylates, and Triphenylphosphine

被引:21
作者
Anary-Abbasinejad, Mohammad [1 ]
Mosslemin, Mohammad H. [1 ]
Hassanabadi, Alireza [1 ]
Tabatabaee, Masoumeh [1 ]
机构
[1] Islamic Azad Univ, Dept Chem, Yazd Branch, Yazd, Iran
关键词
Addition reaction; dialkyl acetylenedicarboxylates; N-aminorhodanine; triphenylphosphine;
D O I
10.1080/00397910802213760
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Protonation of the reactive zwitterionic intermediate produced from the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by N-aminorhodanine followed by the addition of the conjugate anion of N-aminorhodanine on the produced vinylphosphonium cation leads to alkyl (5-oxo-2-thioxo-[1,3,4]thiadiazinan-6-ylidene)acetates in good yields.
引用
收藏
页码:3700 / 3705
页数:6
相关论文
共 14 条
[1]   A three-component reaction between trialkyl phosphites or triphenylphosphine, dimethyl acetylenedicarboxylate and N-aryl-3-hydroxynaphthalene-2-carboxamide [J].
Anary-Abbasinejad, Mohammad ;
Hassanabadi, Alireza ;
Mazraeh-Seffid, Manouchehr .
JOURNAL OF CHEMICAL RESEARCH, 2007, (12) :708-712
[2]  
Anary-Abbasinejad M, 2007, J CHEM RES, P605
[3]  
Anary-Abbasinejad M, 2007, J CHEM RES, P574
[4]  
Anary-Abbasinejad M, 2007, J CHEM RES, P291
[5]  
Anary-Abbasinejad M, 2007, J CHEM RES, P475
[6]  
Anary-Abbasinejad M, 2007, J CHEM RES, P455
[7]  
Anary-Abbasinejad M, 2007, J CHEM RES, P11
[8]   Three-component reaction of triphenylphosphine, acetylenic esters, and aromatic amides: The synthesis of stable nitrogen-containing phosphorus ylides [J].
Anary-Abbasinejad, Mohammad ;
Thhhan, Sakkineh .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (02) :315-319
[9]  
Corbridge D. E. C., 1995, Phosphorus an Outline of the Chemistry, Biochemistry, and Uses
[10]   Triphenylphosphine promoted addition of dimethyl acetylenedicarboxylate to 1,2-benzoquinones: facile synthesis of novel gamma-spirolactones [J].
Nair, V ;
Nair, JS ;
Vinod, AU ;
Rath, NP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3129-3130