Synthesis of 2',4-Dibromo-2,4'-bithiazole Using Novel Long-range Halogen Dance Reaction

被引：2

作者：

Arimitsu, Kenji ^{[1
]}

Hirokawa, Yoshimi ^{[1
]}

Ikegawa, Yuriko ^{[1
]}

Tanba, Akiko ^{[1
]}

Ueda, Yuki ^{[1
]}

Kashihara, Taiga ^{[1
]}

Atarashi, Naruhiro ^{[1
]}

Yoshida, Ryoto ^{[1
]}

Matsuo, Yosuke ^{[1
]}

Maezaki, Naoyoshi ^{[1
]}

机构：

[1] Osaka Ohtani Univ, Fac Pharm, 3-11-1 Nishikiori Kita, Tondabayashi, Osaka 5848540, Japan

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 32期

关键词：

4,5-dibromobithiazole; 1,6-halogen shift; lithium hexamethyldisilazide; long-range halogen dance reaction; nonsymmetric brominated bithiazole; CO-OLIGOMERS; THIAZOLES;

D O I：

10.1002/slct.202302632

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This study presents a novel halogen dance reaction using 4,5-dibromo-2,4'-bithiazole, which demonstrates a long-range effect. The reaction involves the migration of a bromo group from the C5-position to the C2'-position of another thiazole ring when treated with lithium hexamethyldisilazide (LiHMDS), resulting in the formation of a non-symmetric brominated bithiazole. In contrast, the base-induced C2'-bromination of 4-bromobithiazole was found to be inefficient in synthesizing the desired brominated bithiazole due to its poor deprotonation selectivity.

引用

页数：4

共 39 条

[1] n-Type organic field-effect transistors with very high electron mobility based on thiazole oligomers with trifluoromethylphenyl groups
Ando, S
Murakami, R
Nishida, J
Tada, H
Inoue, Y
Tokito, S
Yamashita, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) : 14996 - 14997
[2] Thiopeptide Antibiotic Biosynthesis
Arndt, Hans-Dieter
Schoof, Sebastian
Lu, Jin-Yong
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6770 - 6773
[3] Evidence for "Halogen-Dance" and Ring-Exchange Reactions in Chloro-methylthio-ferrocenes
Blockhaus, Tobias
Bernhartzeder, Stefanie
Kempinger, Werner
Klein-Hessling, Christian
Weigand, Stefan
Suenkel, Karlheinz
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (42) : 6576 - 6587
[4] BASE-CATALYZED HALOGEN DANCE, AND OTHER REACTIONS OF ARYL HALIDES
BUNNETT, JF
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (04) : 139 - &
[5] Cao J, 2003, CHEM MATER, V15, P404, DOI 10.1021/cm020774
[6] Recent progress of halogen-dance reactions in heterocycles
Duan, XF
Zhang, ZB
[J]. HETEROCYCLES, 2005, 65 (08) : 2005 - 2012
[7] Halogen 'dance': a way to extend the boundaries of arene deprotolithiation
Erb, William
Mongin, Florence
[J]. TETRAHEDRON, 2016, 72 (33) : 4973 - 4988
[8] Dramatically different charge transport properties of bisthienyl diketopyrrolopyrrole-bithiazole copolymers synthesized via two direct (hetero)arylation polymerization routes
Guo, Chang
Quinn, Jesse
Sun, Bin
Li, Yuning
[J]. POLYMER CHEMISTRY, 2016, 7 (27) : 4515 - 4524
[9] Anion control of ligand self-recognition in a triple helical array
Harding, LP
Jeffery, JC
Riis-Johannessen, T
Rice, CR
Zeng, ZT
[J]. CHEMICAL COMMUNICATIONS, 2004, (06) : 654 - 655
[10] Potassium carbonate-silica: a highly effective stationary phase for the chromatographic removal of organotin impurities
Harrowven, David C.
Curran, Dennis P.
Kostiuk, Sarah L.
Wallis-Guy, Ian L.
Whiting, Sally
Stenning, Kerri J.
Tang, Bencan
Packard, Emma
Nanson, Lana
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (34) : 6335 - 6337

← 1 2 3 4 →