Open Access
Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions
Timofey Chmovzh
1
,
Ekaterina Knyazeva
1, 2
,
Ekaterina A Knyazeva
1, 2
,
Konstantin Lyssenko
3
,
Vadim Popov
2
,
Vadim V Popov
2
,
Oleg Rakitin
1, 2
,
Oleg A. Rakitin
1, 2
1
Тип публикации: Journal Article
Дата публикации: 2018-10-09
PubMed ID:
30304797
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Краткое описание
A safe and efficient synthesis of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine from the commercial diaminomaleonitrile is reported. Conditions for selective aromatic nucleophilic substitution of one or two bromine atoms by oxygen and nitrogen nucleophiles are found, whereas thiols formed the bis-derivatives only. Buchwald-Hartwig or Ullmann techniques are successful for incorporation of a weak nitrogen base, such as carbazole, into the [1,2,5]thiadiazolo[3,4-d]pyridazine core. The formation of rather stable S…η2-(N=N) bound chains in 4,7-bis(alkylthio)-[1,2,5]thiadiazolo[3,4-d]pyridines makes these compounds promising for the design of liquid crystals.
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Chmovzh T. et al. Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions // Molecules. 2018. Vol. 23. No. 10. p. 2576.
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Chmovzh T., Chmovzh T. N., Knyazeva E., Knyazeva E. A., Lyssenko K., Lyssenko K. A., Popov V., Popov V. V., Rakitin O., Rakitin O. A. Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions // Molecules. 2018. Vol. 23. No. 10. p. 2576.
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TY - JOUR
DO - 10.3390/molecules23102576
UR - https://www.mdpi.com/1420-3049/23/10/2576
TI - Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions
T2 - Molecules
AU - Chmovzh, Timofey
AU - Chmovzh, Timofey N
AU - Knyazeva, Ekaterina
AU - Knyazeva, Ekaterina A
AU - Lyssenko, Konstantin
AU - Lyssenko, Konstantin A.
AU - Popov, Vadim
AU - Popov, Vadim V
AU - Rakitin, Oleg
AU - Rakitin, Oleg A.
PY - 2018
DA - 2018/10/09
PB - MDPI
SP - 2576
IS - 10
VL - 23
PMID - 30304797
SN - 1420-3049
ER -
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@article{2018_Chmovzh,
author = {Timofey Chmovzh and Timofey N Chmovzh and Ekaterina Knyazeva and Ekaterina A Knyazeva and Konstantin Lyssenko and Konstantin A. Lyssenko and Vadim Popov and Vadim V Popov and Oleg Rakitin and Oleg A. Rakitin},
title = {Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions},
journal = {Molecules},
year = {2018},
volume = {23},
publisher = {MDPI},
month = {oct},
url = {https://www.mdpi.com/1420-3049/23/10/2576},
number = {10},
pages = {2576},
doi = {10.3390/molecules23102576}
}
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MLA
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Chmovzh, Timofey, et al. “Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions.” Molecules, vol. 23, no. 10, Oct. 2018, p. 2576. https://www.mdpi.com/1420-3049/23/10/2576.
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