Cyanuric Chloride Catalysed Rapid Conversion of β-Ketoesters into β-Enaminoesters under Mild and Solvent-Free Conditions

被引：6
作者：
Kamble, V. T. [1 ]
Joshi, N. S. [1 ]
Atkore, S. T. [1 ]
机构：
[1] Swami Ramanand Teerth Marathwada Univ, Sch Chem Sci, Organ Chem Res Lab, Nanded 431606, Maharashtra, India
来源：
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2011年 / 8卷 / 03期
关键词：
Amines; beta-Enaminoesters; beta-Ketoesters; Cyanuric chloride; CARBOXYLIC-ACIDS; AZA-ANNULATION; DIASTEREOSELECTIVE REDUCTION; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; BLAISE REACTION; AMINO; ESTERS; DERIVATIVES;
D O I：
10.1007/BF03245892
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cyanuric chloride is shown to be an extremely efficient catalyst for the synthesis of beta-enaminoesters from beta-ketoesters under solvent-free conditions by grinding in a mortar with pestle at 25 degrees C. A short reaction time, an inexpensive and easily available catalyst, mild reaction conditions and excellent yields of the products are attractive features of this methodology.
引用
收藏
页码：616 / 621
页数：6
相关论文
共 60 条
[11]  
Bird TGC, 1996, BIOORG MED CHEM LETT, V6, P515
[12]   Chiral cyclic beta-amino esters .2. Synthesis by diastereoselective reduction of enamino esters [J].
Blot, J ;
Bardou, A ;
Bellec, C ;
FargeauBellassoued, MC ;
Celerier, JP ;
Lhommet, G ;
Gardette, D ;
Gramain, JC .
TETRAHEDRON LETTERS, 1997, 38 (49) :8511-8514
[13]   A new, mild preparation of sulfonyl chlorides [J].
Blotny, G .
TETRAHEDRON LETTERS, 2003, 44 (07) :1499-1501
[14]  
BRUNERIE P, 1985, SYNTHESIS-STUTTGART, P735
[15]   Chiral heterocyclic β-enamino esters:: convenient synthesis and diastereoselective reduction [J].
Calvet, S ;
David, O ;
Vanucci-Bacqué, C ;
Fargeau-Bellassoued, MC ;
Lhommet, G .
TETRAHEDRON, 2003, 59 (33) :6333-6339
[16]   CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION [J].
COOK, GR ;
BEHOLZ, LG ;
STILLE, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3575-3584
[17]   Enantioselective access to five- and six-membered nitrogen-containing heterocycles, based on the asymmetric Michael addition of chiral imines and chiral enamino esters [J].
d'Angelo, J ;
Cave, C ;
Desmaele, D ;
Gassama, A ;
Thominiaux, C ;
Riche, C .
HETEROCYCLES, 1998, 47 (02) :725-746
[18]   A novel asymmetric synthesis of 2,5-dialkylpyrrolidines [J].
Daley, V ;
D'Angelo, J ;
Cavé, C ;
Mahuteau, J ;
Chiaroni, A ;
Riche, C .
TETRAHEDRON LETTERS, 1999, 40 (09) :1657-1660
[19]   SYNTHESIS AND BIOLOGICAL EVALUATION OF DE-AB-CAMPTOTHECIN [J].
DANISHEF.S ;
ETHEREDG.SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3430-3432
[20]   Enamino ester reduction:: A short enantioselective route to pyrrolizidine and indolizidine alkaloids.: Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol [J].
David, O ;
Blot, J ;
Bellec, C ;
Fargeau-Bellassoued, MC ;
Haviari, G ;
Célérier, JP ;
Lhommet, G ;
Gramain, JC ;
Gardette, D .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3122-3131
123456