Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions
Timofey N Chmovzh
1, 2
,
Ekaterina A Knyazeva
1, 3
,
Ludmila V. Mikhalchenko
1, 2
,
Ivan S Golovanov
1
,
Stanislav A. Amelichev
1, 2
,
Oleg A. Rakitin
1, 2, 3, 4
3
Publication type: Journal Article
Publication date: 2018-09-25
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient synthesis of 4,7‐dibromo[1,2,5]thiadiazolo[3,4‐d]pyridazine is reported. For the first time, palladium‐catalysed cross‐coupling reactions of a dihalo derivative was found to be a powerful tool for the selective formation of various mono‐ and diarylated derivatives of strongly electron‐accepting heterocycles. Suzuki–Miyaura coupling can be successfully employed for the preparation of mono‐arylated derivatives, whereas Stille coupling is useful for both mono‐ and diaryl(hetaryl)ated heterocycles. The cyclic voltammogram showed that 4,7‐dibromo[1,2,5]thiadiazolo[3,4‐d]pyridazine can be easily oxidized to form a stable anion radical. The calculated values of ELUMO confirmed that [1,2,5]thiadiazolo[3,4‐d]pyridazine is one of the strongest electron–acceptor systems.
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Chmovzh T. N. et al. Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions // European Journal of Organic Chemistry. 2018. Vol. 2018. No. 41. pp. 5668-5677.
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Chmovzh T. N., Knyazeva E. A., Mikhalchenko L. V., Golovanov I. S., Amelichev S. A., Rakitin O. A. Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions // European Journal of Organic Chemistry. 2018. Vol. 2018. No. 41. pp. 5668-5677.
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TY - JOUR
DO - 10.1002/ejoc.201800961
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201800961
TI - Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions
T2 - European Journal of Organic Chemistry
AU - Chmovzh, Timofey N
AU - Knyazeva, Ekaterina A
AU - Mikhalchenko, Ludmila V.
AU - Golovanov, Ivan S
AU - Amelichev, Stanislav A.
AU - Rakitin, Oleg A.
PY - 2018
DA - 2018/09/25
PB - Wiley
SP - 5668-5677
IS - 41
VL - 2018
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2018_Chmovzh,
author = {Timofey N Chmovzh and Ekaterina A Knyazeva and Ludmila V. Mikhalchenko and Ivan S Golovanov and Stanislav A. Amelichev and Oleg A. Rakitin},
title = {Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions},
journal = {European Journal of Organic Chemistry},
year = {2018},
volume = {2018},
publisher = {Wiley},
month = {sep},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201800961},
number = {41},
pages = {5668--5677},
doi = {10.1002/ejoc.201800961}
}
Cite this
MLA
Copy
Chmovzh, Timofey N., et al. “Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions.” European Journal of Organic Chemistry, vol. 2018, no. 41, Sep. 2018, pp. 5668-5677. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201800961.