The conversion of aryl and heteroaryl methylketones to the corresponding secondary or tertiary amides

被引:8
作者
Ding, Jiaoyang [1 ]
Cao, Liping [1 ]
Wang, Jungang [1 ]
Xue, Weijian [1 ]
Zhu, Yanping [1 ]
Wu, Anxin [1 ]
机构
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金;
关键词
iodine; amide; water; Lieben iodoform reaction; BECKMANN REARRANGEMENT; BOND-CLEAVAGE; AMINES; EFFICIENT; ALCOHOLS; KETONES; AMIDATION; ALDEHYDES; ROUTE; ACIDS;
D O I
10.3184/174751911X13053065216840
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Secondary or tertiary amides have been prepared directly from aryl, heteroaryl methyl ketones using an iodine-amine-NaOH system which afforded the expected products in good yields in an aqueous medium. The present method has the advantages of using inexpensive reagents, mild reaction condition and ease of manipulation.
引用
收藏
页码:298 / 301
页数:4
相关论文
共 51 条
[1]   Stereoselective Rh-catalyzed hydrogenation of cyclobutyl chiral enamides:: Double stereodifferentiation vs catalyst-controlled diastereoselection [J].
Aguado, GP ;
Moglioni, AG ;
García-Expósito, E ;
Branchadell, V ;
Ortuño, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7971-7978
[2]   First observation of Chapman rearrangement of a pseudosaccharyl ether in the solid state:: the thermal isomerization of 3-(methoxy)1,2-benzisothiazole 1,1-dioxide revisited [J].
Almeida, R. ;
Gomez-Zavaglia, A. ;
Kaczor, A. ;
Cristiano, M. L. S. ;
Eusebio, M. E. S. ;
Maria, T. M. R. ;
Fausto, R. .
TETRAHEDRON, 2008, 64 (15) :3296-3305
[3]  
[Anonymous], 1870, JUSTUS LIEBIGS ANN S
[4]   FeCl3-catalyzed Ritter reaction. Synthesis of amides [J].
Anxionnat, Bruno ;
Guerinot, Amandine ;
Reymond, Sebastien ;
Cossy, Janine .
TETRAHEDRON LETTERS, 2009, 50 (26) :3470-3473
[5]   An Efficient and Scalable Ritter Reaction for the Synthesis of tert-Butyl Amides [J].
Baum, Jean C. ;
Milne, Jacqueline E. ;
Murry, Jerry A. ;
Thiel, Oliver R. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05) :2207-2209
[6]   DOES FORMAL INTRAMOLECULAR TRANSFER OF AN ACIDIC DEUTERIUM TO A SITE OF HALOGEN LITHIUM EXCHANGE SHOW THAT LITHIUM HALOGEN EXCHANGE IS FASTER THAN LOSS OF THE ACIDIC DEUTERIUM - EVIDENCE IN FAVOR OF AN ALTERNATIVE MECHANISM [J].
BEAK, P ;
MUSICK, TJ ;
CHEN, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3538-3542
[7]   Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia [J].
Cao, Liping ;
Ding, Jiaoyang ;
Gao, Meng ;
Wang, Zihua ;
Li, Juan ;
Wu, Anxin .
ORGANIC LETTERS, 2009, 11 (17) :3810-3813
[8]  
CHEOL KY, 1999, J HETEROCYCLIC CHEM, V36, P911
[9]   Ammonium salts from polymer-bound N-hydroxysuccinimide as solid-supported reagents for EDC-mediated amidations [J].
Chinchilla, R ;
Dodsworth, DJ ;
Nájera, C ;
Soriano, JM .
TETRAHEDRON LETTERS, 2003, 44 (03) :463-466
[10]   The first catalytic, asymmetric α-additions of isocyanides.: Lewis-base-catalyzed, enantioselective Passerini-type reactions [J].
Denmark, SE ;
Fan, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7825-7827