Mitsunobu type C-N bond formation with 4,7-dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione (DHTD), a new cyclic azodicarboxamide

被引:9
作者
Tsunoda, T [1 ]
Kawamura, Y [1 ]
Uemoto, K [1 ]
Ito, S [1 ]
机构
[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 770, Japan
关键词
D O I
10.3987/COM-97-S(N)78
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combination of 4,7-dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione (DHTD) and tributylphosphine (TBP) was found to mediate successfully C-N bond formation between N-methyltosylamide, a typical N-nucleophile, and several alcohols of different structural types. The unique feature of this combination is that it activates the reaction of sec-alcohols at room temperature.
引用
收藏
页码:177 / 179
页数:3
相关论文
共 12 条
[1]  
COOKSON RC, 1962, TETRAHEDRON LETT, P615
[2]  
DAUPHIN G, 1961, B SOC CHIM FR, P486
[3]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]
[4]   CLEAVAGE OF SULFONAMIDES WITH SODIUM NAPHTHALENE [J].
JI, S ;
GORTLER, LB ;
WARING, A ;
BATTISTI, A ;
BANK, S ;
CLOSSON, WD ;
WRIEDE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5311-&
[5]   INVESTIGATION ON SODIUM-LIQUID AMMONIA CLEAVAGE OF A TOSYL PROTECTING GROUP OF TOSYLAMINO ACIDS AND PEPTIDES [J].
KOVACS, J ;
GHATAK, UR .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :119-&
[6]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[7]   CONVERSION OF ALCOHOLS INTO HALOALKANES IN TERTIARY PHOSPHINE METHYL HALIDE 4-METHYL-1,2,4-TRIAZOLIDINE-3,5-DIONE (MTAD) SYSTEM [J].
OSHIKAWA, T ;
YAMASHITA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (09) :2675-2676
[8]   NOVEL REACTIVITY OF STABILIZED METHYLENETRIBUTYLPHOSPHORANE - A NEW MITSUNOBU REAGENT [J].
TSUNODA, T ;
OZAKI, F ;
ITO, S .
TETRAHEDRON LETTERS, 1994, 35 (28) :5081-5082
[9]   Mitsunobu-type alkylation with active methine compounds [J].
Tsunoda, T ;
Nagino, C ;
Oguri, M ;
Ito, S .
TETRAHEDRON LETTERS, 1996, 37 (14) :2459-2462
[10]   N,N,N',N'-TETRAMETHYLAZODICARBOXAMIDE (TMAD), A NEW VERSATILE REAGENT FOR MITSUNOBU REACTION - ITS APPLICATION TO SYNTHESIS OF SECONDARY-AMINES [J].
TSUNODA, T ;
OTSUKA, J ;
YAMAMIYA, Y ;
ITO, S .
CHEMISTRY LETTERS, 1994, (03) :539-542