On the reaction of chloroalkylbenzothiazoles with alkoxides

被引:10
作者
Florio, S
Capriati, V
Colli, G
机构
[1] Dipartimento Farmaco-Chimico, Università di Bari, 70125 Bari
关键词
D O I
10.1016/S0040-4020(97)00243-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-chloroalkylbenzothiazoles 1a-c react with alkoxides to give substitution and ring-expanded products 3 and 4. The substitution ring-enlargement competition much depends upon the solvent. the substitution reaction being preferred in alcohols and the ring-enlargement in DMF. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5839 / 5846
页数:8
相关论文
共 29 条
[1]   AN EFFICIENT SYNTHESIS OF 2-(HALOGENOMETHYL)PENEMS [J].
ALTAMURA, M ;
PERROTTA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :272-274
[2]   RING-OPENING IN A NON-BASIC MEDIUM OF 2-METHYL-6-NITROBENZOTHIAZOLE AND H-D EXCHANGE AT THE 2-METHYL PROMOTED BY SILVER(I) [J].
ARESTA, M ;
CIMINALE, F .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1981, (07) :1520-1523
[3]   STEREOSELECTIVE ALDOL CONDENSATION OF 3,4-DIHYDRO-3-OXO-2H-1,4-BENZOTHIAZINES - X-RAY DETERMINATION OF THE ALDOL STEREOSTRUCTURE [J].
BABUDRI, F ;
FLORIO, S ;
ZUCCARO, L .
TETRAHEDRON, 1985, 41 (03) :569-573
[4]  
BABUDRI F, 1986, HETEROCYCLES, V24, P2215
[5]  
CHIKASHITA H, 1986, SYNTHESIS-STUTTGART, P375
[6]  
COREY EJ, 1978, TETRAHEDRON LETT, V1, P13
[7]   THIAZOLYLMETHYLENETRIPHENYLPHOSPORANE AND ITS BENZO DERIVATIVE - STABLE AND PRACTICAL WITTIG REAGENTS FOR THE SYNTHESIS OF VINYLTHIAZOLES AND VINYLBENZOTHIAZOLES - 2-CARBON HOMOLOGATION OF ALDEHYDES [J].
DONDONI, A ;
FANTIN, G ;
FOGAGNOLO, M ;
MEDICI, A ;
PEDRINI, P .
TETRAHEDRON, 1988, 44 (07) :2021-2031
[8]   DIASTEREOSELECTIVE ALDOL CONDENSATION OF 2-METALLOALKYL-BENZOTHYAZOLES [J].
EPIFANI, E ;
FLORIO, S ;
INGROSSO, G .
TETRAHEDRON, 1987, 43 (08) :1937-1942
[9]   COUPLING OF EPOXIDES WITH 2-BENZOTHIAZOLYLALKYLLITHIUMS [J].
EPIFANI, E ;
FLORIO, S ;
FAVA, GG .
TETRAHEDRON, 1990, 46 (24) :8169-8178
[10]   REGIOSELECTIVE CONTROL OF ALLYLLITHIUMS OF SOME HETEROCYCLES - ALPHA-VS-GAMMA CONDENSATION WITH ALDEHYDES [J].
EPIFANI, E ;
FLORIO, S ;
INGROSSO, G .
TETRAHEDRON LETTERS, 1987, 28 (50) :6385-6388