Efficient general synthesis of 1-(benzotriazol-1-yl)alkyl esters

被引:56
作者
Katritzky, AR [1 ]
Pastor, A [1 ]
Voronkov, MV [1 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
关键词
D O I
10.1002/jhet.5570360333
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-(Benzotriazol-1-yl)alkyl esters 2a-u were obtained in yields averaging 86% by the direct reaction of various aldehydes with the corresponding N-acylbenzotriazoles in the presence of a catalytic amount of potassium carbonate (10-25 mole %). The procedure was optimized by evaluating the effects of solvent, catalyst, temperature and other parameters.
引用
收藏
页码:777 / 781
页数:5
相关论文
共 22 条
[1]   N-[1-(ACYLOXY)ALKYL]HETEROARYLIUM SALTS IN SYNTHESIS .3. INTRAMOLECULAR ORTHO-ACYLATION OF SOME N-HETEROAROMATIC RING-SYSTEMS [J].
ANDERS, E ;
BOLDT, HG ;
CLARK, T ;
FUCHS, R ;
GASSNER, T .
CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (01) :279-296
[2]   CHLOROACYLATION AND BROMOACYLATION OF CARBONYL-COMPOUNDS .4. INVESTIGATIONS OF REACTION-MECHANISM [J].
BIGLER, P ;
NEUENSCHWANDER, M .
HELVETICA CHIMICA ACTA, 1978, 61 (07) :2381-2396
[3]   A GENERAL PREPARATION OF HIGHLY FUNCTIONALIZED ZINC AND COPPER ORGANOMETALLICS AT THE ALPHA-POSITION TO AN OXYGEN [J].
CHOU, TS ;
KNOCHEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4791-4793
[4]   APPLICATION OF PHASE-TRANSFER CATALYSIS TO THE CHEMICAL MODIFICATION OF CROSS-LINKED POLYSTYRENE RESINS [J].
FRECHET, JMJ ;
DESMET, MD ;
FARRALL, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) :1774-1779
[5]  
FRENCH HE, 1921, J AM CHEM SOC, V43, P650
[6]   REACTIONS OF CARBINOLAMINES .2. ACYLATION OF 1-HYDROXYMETHYL-1H-BENZOTRIAZOLE [J].
GAYLORD, NG ;
NAUGHTON, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (09) :1022-1024
[7]  
KATNITZKY AR, 1995, J ORG CHEM, V60, P7625
[8]   BENZOTRIAZOLE-MEDIATED CONVERSIONS OF AROMATIC AND HETEROAROMATIC ALDEHYDES TO FUNCTIONALIZED KETONES [J].
KATRITZKY, AR ;
LANG, HY ;
WANG, ZQ ;
ZHANG, ZX ;
SONG, HM .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7619-7624
[9]   SULFONYL DERIVATIVES OF BENZOTRIAZOLE .1. A NOVEL-APPROACH TO THE ACTIVATION OF CARBOXYLIC-ACIDS [J].
KATRITZKY, AR ;
SHOBANA, N ;
PERNAK, J ;
AFRIDI, AS ;
FAN, WQ .
TETRAHEDRON, 1992, 48 (37) :7817-7822
[10]   NOVEL AND CONVENIENT ROUTES TO FUNCTIONALIZED ALKYNYL KETONES FROM 1-(BENZOTRIAZOL-1-YL)PROPARGYL ETHYL ETHERS [J].
KATRITZKY, AR ;
LANG, HY .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7612-7618