New and efficient synthesis of dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)-2-oxoethyl]malonates

被引:70
作者
Shaabani, A
Yavari, I
Teimouri, MB
Bazgir, A
Bijanzadeh, HR
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Chem, Tehran, Iran
关键词
dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)-2-oxoethyl]malonates; Meldrum's acid; 4-nitrobenzaldehyde;
D O I
10.1016/S0040-4020(00)01122-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The condensation product of Meldrum's acid and 4-nitrobenzaldehyde reacts smoothly with alkyl isocyanides in the presence of alcohols to produce dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)-2-oxoethyl]malonates in excellent yield. This reaction provides a useful synthetic route to highly functionalized amidodiesters. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1375 / 1378
页数:4
相关论文
共 10 条
[1]   A SPECTACULAR EXAMPLE OF THE IMPORTANCE OF ROTATIONAL BARRIERS - THE IONIZATION OF MELDRUMS ACID [J].
ARNETT, EM ;
HARRELSON, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :809-812
[2]  
BECKWITH ALJ, 1970, CHEM FUNCTIONAL GROU, P74
[3]  
CELERIER JP, 1983, SYNTHESIS-STUTTGART, P195
[4]  
CHEN BC, 1978, HETROCYCLES, V7, P345
[5]   THE STRUCTURE OF MELDRUMS SUPPOSED BETA-LACTONIC ACID [J].
DAVIDSON, D ;
BERNHARD, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (10) :3426-3428
[6]   SOME CONDENSATION REACTIONS OF ISOPROPYLIDENE MALONATE [J].
HEDGE, JA ;
KRUSE, CW ;
SNYDER, HR .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (09) :3166-&
[7]   MELDRUMS ACID [J].
MCNAB, H .
CHEMICAL SOCIETY REVIEWS, 1978, 7 (03) :345-358
[8]   A beta-lactonic acid from acetone and malonic acid [J].
Meldrum, AN .
JOURNAL OF THE CHEMICAL SOCIETY, 1908, 93 :598-601
[9]   A NOVEL MICHAEL REACTION OF SILYL ENOL ETHERS VIA HETERO-DIELS-ALDER REACTION WITH ALKYLIDENE-MELDRUMS ACID [J].
MIZUKAMI, S ;
KIHARA, N ;
ENDO, T .
TETRAHEDRON LETTERS, 1993, 34 (46) :7437-7440
[10]   MELDRUMS ACID IN ORGANIC-SYNTHESIS .2. GENERAL AND VERSATILE SYNTHESIS OF BETA-KETO-ESTERS [J].
OIKAWA, Y ;
SUGANO, K ;
YONEMITSU, O .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :2087-2088