N-alkylation of phthalimide, carboxamide, and sulfonamides by oxidation-reduction condensation using di-tert-butyl-1,4-benzoquinone and alkyl diphenylphosphinite

被引:17
作者
Mukaiyama, T
Aoki, H
机构
[1] Kitasato Inst, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
[2] Kitasato Univ, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan
关键词
D O I
10.1246/cl.2005.142
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Various N-atkylamides were obtained in high yields under mild conditions by treating alkyl diphenylphosphinite with phthalimide. carboxamide or sulfonamides in the presence of 2,6-di-tert-butvi- 1,4-benzoqui none (DBBQ) by oxdation-reduction condensation.
引用
收藏
页码:142 / 143
页数:2
相关论文
共 16 条
[1]   N-alkylation of 1H-indoles and 9H-carbazoles with alcohols [J].
Bombrun, A ;
Casi, G .
TETRAHEDRON LETTERS, 2002, 43 (12) :2187-2190
[2]   USE OF THE MITSUNOBU REACTION IN THE SYNTHESIS OF POLYAMINES [J].
EDWARDS, ML ;
STEMERICK, DM ;
MCCARTHY, JR .
TETRAHEDRON, 1994, 50 (19) :5579-5590
[3]   New Mitsunobu reagents in the C-C bond formation.: Application to natural product synthesis [J].
Itô, S ;
Tsunoda, T .
PURE AND APPLIED CHEMISTRY, 1999, 71 (06) :1053-1057
[4]  
Jia ZZJ, 1999, SYNLETT, P565
[5]  
KOPPEL I, 1994, J CHEM RES-S, P212
[6]   ACIDITY OF IMIDODICARBONATES AND TOSYLCARBAMATES IN DIMETHYL-SULFOXIDE - CORRELATION WITH YIELDS IN THE MITSUNOBU REACTION [J].
KOPPEL, I ;
KOPPEL, J ;
DEGERBECK, F ;
GREHN, L ;
RAGNARSSON, U .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7172-7174
[7]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[8]   A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation [J].
Mukaiyama, T ;
Ikegai, K .
CHEMISTRY LETTERS, 2004, 33 (11) :1522-1523
[9]   Preparation of nitriles from primary alcohols by a new type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and diethyl cyanophosphonate [J].
Mukaiyama, T ;
Masutani, K ;
Hagiwara, Y .
CHEMISTRY LETTERS, 2004, 33 (09) :1192-1193
[10]   A convenient method for the preparation of inverted tert-alkyl carboxylates from chiral tert-alcohols by a new type of oxidation-reduction, condensation using 2,6-dimethyl-1,4-benzoquinone [J].
Mukaiyama, T ;
Shintou, T ;
Fukumoto, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) :10538-10539