The nitration and bromination of 2-(pentafluorosulfanyl)-1,3-benzothiazole and 2-(trifluoromethyl)-1,3-benzothiazole

被引：0

作者：

Guzyr, Olexandr I. ^{[1
]}

Potikha, Lyudmila M. ^{[1
,2
]}

Shishkina, Svitlana V. ^{[3
]}

Fetyukhin, Volodymyr N. ^{[4
]}

Shermolovich, Yuriy G. ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Akad Kukharya St, UA-02660 Kiev, Ukraine

[2] Kyiv Taras Shevchenko Natl Univ, 64 Volodymyrska St, UA-01033 Kiev, Ukraine

[3] Natl Acad Sci Ukraine, State Sci Inst, Inst Single Crystals, 60 Nauky Ave, UA-61001 Kharkiv, Ukraine

[4] Life Chem Inc, 1A Dixie Ave, Niagara On The Lake, ON L0S 1J0, Canada

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2023年 / 59卷 / 4-5期

关键词：

benzothiazole; pentafluoropersulfurans; 2-(pentafluorosulfanyl)-1,3-benzothiazole; 2-(trifluoromethyl)-1,3-benzothiazole; bromination; nitration; CONTAINING CYANINE DYES; BENZOTHIAZOLES; DERIVATIVES;

D O I：

10.1007/s10593-023-03197-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nitration and halogenation reactions of 2-(pentafluorosulfanyl)- and 2-(trifluoromethyl)-1,3-benzothiazoles were studied. Methods for the preparation of previously undescribed mononitro-substituted 1,3-benzothiazoles (4-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole, 4-nitro-2-(trifluoromethyl)-1,3-benzothiazole, and 6-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole) as well as a new method for the synthesis of the previously known 6-nitro-2-(trifluoromethyl)-1,3-benzothiazole were developed. The procedure involved the reaction of 2-(trifluoromethyl)-1,3-benzothiazole with NH4NO3 in TFAA at room temperature. An efficient method for the preparation of 2-substituted 4,5,6,7-tetrabromo-1,3-benzothiazoles based on the reaction of 2-substituted 1,3-benzothiazoles with NBS in TFA-H2SO4 at room temperature was proposed.

引用

页码：304 / 308

页数：5

共 50 条

[1] The nitration and bromination of 2-(pentafluorosulfanyl)-1,3-benzothiazole and 2-(trifluoromethyl)-1,3-benzothiazole
Olexandr I. Guzyr
Lyudmila M. Potikha
Svitlana V. Shishkina
Volodymyr N. Fetyukhin
Yuriy G. Shermolovich
Chemistry of Heterocyclic Compounds, 2023, 59 : 304 - 308
[2] 2-(2-Nitrophenyl)-1,3-benzothiazole
Vijayakumar, S.
Murugavel, S.
Selvakumar, R.
Bakthadoss, M.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : 02362 - +
[3] 2-(2-Pyrrolyl)-1,3-benzothiazole
Davidovic, Naka
Matkovic-Calogovic, Dubravka
Popovic, Zora
Fiser-Jakic, Lelja
Acta Crystallographica, Section C: Crystal Structure Communications, 1999, 55 (pt 1): : 119 - 120
[4] 2-(1-Piperidinyl)-1,3-benzothiazole
Alvarez, RG
Kennedy, AR
Khalaf, AI
Suckling, CJ
Waigh, RD
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2005, 61 : O569 - O570
[5] 2-(2-pyrrolyl)-1,3-benzothiazole
Davidovic, N
Matkovic-Calogovic, D
Popovic, Z
Fiser-Jakic, L
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1999, 55 : 119 - 120
[6] 2-(4-Aminophenyl)-1,3-benzothiazole
Zhang, Yong
Su, Zhen-Hong
Wang, Qing-Zhi
Teng, Lei
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O2065 - U1440
[7] 2-(2,4,5-trimethoxyphenyl)-1,3-benzothiazole
Chen, Lian-Qing
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3395 - U2400
[8] 2-(4-amino-3-iodophenyl)-1,3-benzothiazole
Wang, Wu-Shang
Gao, Min
Chen, Xiangji
Liu, Boli
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O5668 - O5669
[9] 2-(2H-1,3-Benzodioxol-5-yl)-1,3-benzothiazole
Lakshmanan, D.
Murugavel, S.
Selvakumar, R.
Bakthadoss, M.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O960 - +
[10] Synthesis and structures of photoactive manganese-carbonyl complexes derived from 2-(pyridin-2-yl)-1,3-benzothiazole and 2-(quinolin-2-yl)-1,3-benzothiazole
Stenger-Smith, Jenny
Chakraborty, Indranil
Carrington, Samantha
Mascharak, Pradip
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2017, 73 : 357 - 361

← 1 2 3 4 5 →