SULFONYL DERIVATIVES OF BENZOTRIAZOLE .1. A NOVEL-APPROACH TO THE ACTIVATION OF CARBOXYLIC-ACIDS

被引:65
作者
KATRITZKY, AR
SHOBANA, N
PERNAK, J
AFRIDI, AS
FAN, WQ
机构
[1] Center For Heterocyclic Compounds, Department of Chemistry University of Florida, Gainesville
关键词
D O I
10.1016/S0040-4020(01)80459-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Acylbenzotriazoles (8,R=Me,Et,n-Bu and Ph) are prepared in good yields by fusion of benzotriazole and acid chlorides at 80 - 100-degrees-C. In cases when the corresponding acid chlorides are not available, 1-acylbenzotriazoles are conveniently available from 1-(1-methanesulfonyl)benzotriazole and the respective carboxylic acids as illustrated by the preparation of 2-, 3-, and 4-pyridoyl-, 2-pyrrolylcarbonyl- and 2-furoyl-benzotriazole in yields of 80 - 95%. Preparations of two sulfonyl derivatives of benzotriazole are also described.
引用
收藏
页码:7817 / 7822
页数:6
相关论文
共 31 条
[1]   AZOLIDES .12. C-13 NUCLEAR MAGNETIC-RESONANCE STUDY OF N-METHYL AND N-ACETYL DERIVATIVES OF AZOLES AND BENZAZOLES [J].
BEGTRUP, M ;
CLARAMUNT, RM ;
ELGUERO, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (02) :99-104
[2]  
Bell F, 1926, J CHEM SOC, P954
[3]   PSCHORR CYCLIZATION .2. FURTHER REACTIONS WITH PYRROLE DERIVATIVES [J].
BEVERIDGE, S ;
HUPPATZ, JL .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (06) :1341-+
[4]   THERMAL INTERMOLECULAR EXCHANGE BETWEEN N-ACYLBENZOTRIAZOLES [J].
DRULINER, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) :6879-&
[5]  
FINLEY JH, 1980, Patent No. 9998
[6]   NMR-STUDIES IN THE HETEROCYCLIC SERIES .20. A C-13 NMR-STUDY OF THE STRUCTURES OF N-HYDROXYBENZOTRIAZOLE AND ITS ACYLATED DERIVATIVES [J].
FRUCHIER, A ;
ELGUERO, J ;
HEGARTY, AF ;
MCCARTHY, DG .
ORGANIC MAGNETIC RESONANCE, 1980, 13 (05) :339-342
[7]   STUDY ON ORGANOSILYL AZOLE SERIES .1. ACTION OF ALKYL-HALIDES, ACID-CHLORIDES AND HALOGENATED KETONES [J].
GASPARINI, JP ;
GASSEND, R ;
MAIRE, JC ;
ELGUERO, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 188 (02) :141-150
[8]   ORGANOSTANNYLAZOLES .3. NUCLEOPHILIC-SUBSTITUTION REACTIONS WITH ACID-CHLORIDES AND HALOGENATED KETONES [J].
GASSEND, R ;
MAIRE, JC ;
POMMIER, JC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 137 (02) :185-192
[9]   DISPLACEMENT REACTIONS IN THE BENZOTRIAZOLE SERIES [J].
GAYLORD, NG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (01) :285-287
[10]   DIFFERENTIATION OF NUCLEOPHILIC AND GENERAL BASE CATALYSIS IN THE HYDROLYSIS OF N-ACETYLBENZOTRIAZOLE USING THE PROTON INVENTORY TECHNIQUE [J].
GOPALAKRISHNAN, G ;
HOGG, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4959-4964