Reactions of 4-tosyl-2-phenyl-5-chloro-1,3-thiazole with N-, O-, and S-nucleophiles

被引：0

作者：

K. V. Turov

T. K. Vinogradova

V. S. Brovarets

B. S. Drach

机构：

[1] National Academy of Sciences of Ukraine,Institute of Bioorganic Chemistry and Petrochemistry

来源：

Russian Journal of General Chemistry | 2010年 / 80卷

关键词：

EtOH; NaSH; Tosylates; Thiophenol; Thiazole Ring;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

The accessible two-center electrophilic substrate 4-tosyl-2-phenyl-5-chloro-1,3-thiazole reacts regioselectively with N-, O-, and S-nucleophiles to eliminate a chloride ion. The analog of this substrate, 4-tosyl-2-phenyl-5-p-chlorophenylsulphonyl-1,3-thiazole, reacts with “soft” and “hard” nucleophiles differently: with the participation of C5 or C4 center, respectively, that seems to be caused by the principle of “symbiosis” in the transition state.

引用

页码：825 / 828

页数：3

共 10 条

[1] Reactions of 4-Tosyl-2-phenyl-5-chloro-1,3-thiazole with N-, O-, and S-Nucleophiles
Turov, K. V.
Vinogradova, T. K.
Brovarets, V. S.
Drach, B. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (04) : 825 - 828
[2] Reaction of 2-(Benzenesulfonyl)-5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazole with O-, N-, S-, and C-nucleophiles
K. V. Turov
B. S. Drach
Russian Journal of General Chemistry, 2008, 78 : 629 - 633
[3] Reaction of 2-(Benzenesulfonyl)-5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazole with O-, N-, S-, and C-nucleophiles
Turov, K. V.
Drach, B. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (04) : 629 - 633
[4] Transformations of 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole
Turov, K. V.
Vinogradova, T. K.
Drach, B. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (11) : 2132 - 2136
[5] Transformations of 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole
K. V. Turov
T. K. Vinogradova
B. S. Drach
Russian Journal of General Chemistry, 2008, 78 : 2132 - 2136
[6] Synthesis of 4-tosyl-5-chloro-1,3-thiazole-2-carbonitrile and its transformations
K. V. Turov
T. K. Vinogradova
B. S. Drach
Russian Journal of General Chemistry, 2010, 80 : 117 - 120
[7] Synthesis of 4-tosyl-5-chloro-1,3-thiazole-2-carbonitrile and its transformations
Turov, K. V.
Vinogradova, T. K.
Drach, B. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2010, 80 (01) : 117 - 120
[8] Crystal structure and Hirshfeld surface analysis of 2-(4-chlorophenyl)-4-(dimethoxymethyl)-5-phenyl-1,3-thiazole
Guseinov, Firudin, I
Kobrakov, Konstantin, I
Shuvalova, Elena, V
Tuzharov, Egor, I
Akkurt, Mehmet
Yildirim, Sema Ozturk
Bhattarai, Ajaya
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2022, 78 : 675 - +
[9] Cascade synthesis of 2-amino-5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole by reaction of 4-chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide with thiourea
G. N. Rozentsveig
V. Yu. Serykh
K. A. Chernyshev
I. B. Rozentsveig
G. G. Levkovskaya
L. B. Krivdin
Russian Journal of Organic Chemistry, 2011, 47
[10] Synthesis of new 2,5-diamino-1,3-thiazole and 2-thiohydantoin derivatives by condensation of N-(2-Aryl-1-chloro-2-oxoethyl) carboxamides with thioureas
A. G. Balya
A. N. Chernega
S. A. But
A. N. Vasilenko
V. S. Brovarets
B. S. Drach
Russian Journal of General Chemistry, 2008, 78 : 1427 - 1435

← 1 →