Direct Exchange of Oxygen and Selenium Atoms in the 1,2,5-Oxadiazoles and 1,2,5-Selenadiazoles by Action of Sulfur Monochloride
Abstract
:1. Introduction
2. Results and Discussion
2.1. Conversion of 1,2,5-Oxadiazoles into 1,2,5-Thiadiazoles
No. | Starting Compound | Quantity of Reagents for 1 Equiv of Starting Compound | Temperature, °С | Reaction Time, h | Reaction Product, Yield % | |
---|---|---|---|---|---|---|
S2Cl2 | Pyridine | |||||
1 | 6 | 6 | 8 | 82 | 4 | 5, 76 |
2 | 6 | 3 | 4 | 20 | 20 | 7, 90 |
3 | 6 | 6 | 8 | 20 | 20 | 8, 83 |
4 | 7 | 3 | 4 | 20 | 20 | 8, 66 |
5 | 7 | 6 | 8 | 82 | 5 | 5, 56 |
6 | 8 | 2 | 3 | 82 | 2 | 5, 85 |
2.2. Conversion of 1,2,5-Selenadiazoles into 1,2,5-Thiadiazoles
No. | Starting Compound | Quantity of S2Cl2 for 1 Equiv of Starting Compound | Тemperature, °С | Reaction Time, h | Reaction Product, Yield % |
---|---|---|---|---|---|
1 | 13 | 3 | 20 | 3 | 7, 91 |
2 | 13 | 6 | 100 | 6 | 8, 78 |
3 | 14 | 3 | 20 | 20 | 8, 83 |
4 | 15 | 6 | 100 | 6 | 8, 85 |
5 | 16 | 3 | 20 | 20 | 2, 93 |
6 | 17 | 6 | 100 | 6 | 2, 73 |
7 | 18 | 2 | 70 | 3 | 21, 75 |
8 | 19 | 2 | 20 | 6 | 22, 47 |
9 | 20 | 2 | 70 | 2 | 23, 57 |
3. Experimental Section
3.1. General Information
3.2. General Procedure for the Reaction of 1,2,5-Oxadiazoles with S2Cl2 and Pyridine in Acetonitrile
3.3. General Procedure for the Reaction of 1,2,5-Selenadiazoles with S2Cl2 in DMF
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Konstantinova, L.S.; Knyazeva, E.A.; Rakitin, O.A. Direct Exchange of Oxygen and Selenium Atoms in the 1,2,5-Oxadiazoles and 1,2,5-Selenadiazoles by Action of Sulfur Monochloride. Molecules 2015, 20, 14522-14532. https://doi.org/10.3390/molecules200814522
Konstantinova LS, Knyazeva EA, Rakitin OA. Direct Exchange of Oxygen and Selenium Atoms in the 1,2,5-Oxadiazoles and 1,2,5-Selenadiazoles by Action of Sulfur Monochloride. Molecules. 2015; 20(8):14522-14532. https://doi.org/10.3390/molecules200814522
Chicago/Turabian StyleKonstantinova, Lidia S., Ekaterina A. Knyazeva, and Oleg A. Rakitin. 2015. "Direct Exchange of Oxygen and Selenium Atoms in the 1,2,5-Oxadiazoles and 1,2,5-Selenadiazoles by Action of Sulfur Monochloride" Molecules 20, no. 8: 14522-14532. https://doi.org/10.3390/molecules200814522