Phosphonitrilic chloride as an efficient reagent for the synthesis of β-sultams

被引:4
作者
Zarei, Maaroof [1 ]
机构
[1] Hormozgan Univ, Coll Sci, Dept Chem, Bandar Abbas 71961, Iran
关键词
beta-Sultam; Phosphonitrilic chloride; Sulfene; Schiff base; Cycloaddition; SUBSTITUTED 1,2-THIAZETIDINE 1,1-DIOXIDES; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CYCLOADDITION REACTIONS; BECKMANN REARRANGEMENT; ACID-DERIVATIVES; REACTIVITY; MECHANISM; LACTAMS; SULFONYLATION;
D O I
10.1016/j.tetlet.2012.12.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient route for the conversion of imines and sulfonic acids into beta-sultams using phosphonitrilic chloride at room temperature in dry CH2Cl2 is described. Optimization of the conditions was performed. This method is very convenient and the water-soluble by-product is removed by simple aqueous work-up. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1100 / 1102
页数:3
相关论文
共 58 条
[21]   REACTIONS OF SULFENES WITH SCHIFF-BASES - STEREOCHEMISTRY AND THERMAL FRAGMENTATION OF THIAZETIDINE 1,1-DIOXIDE [J].
HIRAOKA, T ;
KOBAYASHI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (02) :480-483
[22]  
Holleman A. F., 2001, Inorganic Chemistry
[23]   Biological Activity of Some Monocyclic- and Bicyclic β-Lactams with Specified Functional Groups [J].
Hwu, Jih Ru ;
Ethiraj, Krishna S. ;
Hakimelahi, Gholam H. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2003, 3 (04) :305-313
[24]  
Iwama T, 1996, REV HETEROATOM CHEM, V15, P25
[25]   Reactions of a β-sultam ring with Lewis acids via the C-S bond cleavage [J].
Iwama, T ;
Ogawa, M ;
Kataoka, T ;
Muraoka, O ;
Tanabe, G .
TETRAHEDRON, 1998, 54 (31) :8941-8974
[26]   Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt [J].
Jarrahpour, Aliasghar ;
Zarei, Maaroof .
TETRAHEDRON, 2010, 66 (27-28) :5017-5023
[27]   DMF-dimethyl sulfate as a new reagent for the synthesis of β-lactams [J].
Jarrahpour, Aliasghar ;
Zarei, Maaroof .
TETRAHEDRON LETTERS, 2009, 50 (14) :1568-1570
[28]   RETURN OF SULFENES [J].
KING, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (01) :10-17
[29]  
Labarre JF, 1996, SYNLETT, P799
[30]   New synthesis of β-sultams from pentafluorophenyl sulfonates [J].
Lewis, Alexandra K. de K. ;
Mok, B. James ;
Tocher, Derek A. ;
Wilden, Jonathan D. ;
Caddick, Stephen .
ORGANIC LETTERS, 2006, 8 (24) :5513-5515