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 50 条

[21] Synthesis, crystal and molecular structure of 2-phenyl-4-para-nitrophenyl-5-benzyl-1,3-thiazole
Terenteva, NA
Petrov, ML
Potekhin, KA
Struchkov, YT
ZHURNAL OBSHCHEI KHIMII, 1997, 67 (04): : 678 - 680
[22] Cyclocondensation of 1-tosyl-2,2-dichloroethenyl isothiocyanate with O-, S-, N-, and C-nucleophiles
Babii, SB
Zyabrev, VS
Drach, BS
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2002, 72 (11) : 1730 - 1735
[23] Cyclocondensation of 1-Tosyl-2,2-dichloroethenyl Isothiocyanate with O-, S-, N-, and C-Nucleophiles
S. B. Babii
V. S. Zyabrev
B. S. Drach
Russian Journal of General Chemistry, 2002, 72 : 1730 - 1735
[24] Heterobimetallic Pd-Sn Catalysis: Michael Addition Reaction with C-, N-, O-, and S-Nucleophiles and in Situ Diagnostics
Das, Debjit
Pratihar, Sanjay
Roy, Sujit
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06): : 2430 - 2442
[25] Cs2CO3-promoted defluorination and functionalization of α-CF3 carbonyl compounds in the presence of N-, O-, and/or S-nucleophiles
Wu, Yue
Zhang, Bingbing
Zheng, Yinying
Wang, Yuheng
Lei, Xinsheng
RSC ADVANCES, 2018, 8 (29) : 16019 - 16023
[26] SOME CHEMICAL-REACTIONS OF 4-[4'-(1',3'-DIPHENYLPYRAZOLYL)METHYLENE]-2-PHENYL-5-OXO-(4 H)-1,3-THIAZOLE
ELKASCHEF, MA
ABDELMEG.ME
YASSIN, SMA
ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1974, 80 (01): : 119 - 123
[27] D-Allal- and D-Galactal-Derived Vinyl N-Mesylaziridines: Regio- and Stereoselectivity in Addition Reactions of O-, C-, N-, and S-Nucleophiles
Di Bussolo, Valeria
Frau, Ileana
Pineschi, Mauro
Crotti, Paolo
SYNTHESIS-STUTTGART, 2012, 44 (18): : 2863 - 2871
[28] Intramolecular C-H...N and intermolecular N-H...N interactions in 2-amino-4-phenyl-1,3-thiazole
Rajnikant
Dinesh
INDIAN JOURNAL OF PHYSICS, 2004, 78 (07) : 587 - 589
[29] (S)-4-Phenyl-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-1,3-thiazole
Pawar, Sunayna
Bhatt, Pralav
Govender, Thavendran
Kruger, Hendrik G.
Maguire, Glenn E. M.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
[30] Reactions of 2-nitropolyhalodienes with S,S-, O,S- and N,S-nucleophiles to 1,3-oxathiolane, 1,3-thiazolidine and 1,3-dithane and thioether compounds
Ibis, C
Sayil, C
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 106 (1-4): : 29 - 36

← 1 2 3 4 5 →