Microwave-Assisted Asinger Synthesis of Thiazolines †
Abstract
:1. Introduction
2. Results and Discussion
3. Experiment
3.1. Synthesis of Thiazolines under Conventional Conditions—General Procedure
3.2. Synthesis of Thiazolines under Microwave Irradiation Conditions—General Procedure
3.3. 2-(4-Chlorophenyl)-4-methyl-2,5-dihydrothiazole 1
3.4. 2-(2-Chlorophenyl)-4-methyl-2,5-dihydrothiazole 2
3.5. 4-Methyl-2-phenyl-2,5-dihydrothiazole 3
3.6. 4-(4-Methyl-2,5-dihydrothiazol-2-yl)phenol 4
3.7. 4-Methyl-2-(p-tolyl)-2,5-dihydrothiazole 5
3.8. 2-(2,3-Dimethoxyphenyl)-4-methyl-2,5-dihydrothiazole 6
3.9. 2-Methoxy-4-(4-methyl-2,5-dihydrothiazol-2-yl)phenol 7
3.10. 4-Methyl-2-(2-(prop-2-yn-1-yloxy)phenyl)-2,5-dihydrothiazole 8
3.11. 3-Methyl-1-thia-4-azaspiro[4.5]dec-3-ene 9
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Entry | R1 | R2 | R3 | X | Ammonia Source | Solvent | Additive | Reaction Temperature (°C) | Reaction Time (h) | %Yield |
---|---|---|---|---|---|---|---|---|---|---|
1 | Me | Me | Me | Br | NH4OH/H2O | - | NaSH | R. T. | 24 | <5 |
2 | Ph | Me | Me | Br | NH4OH/H2O | - | NaSH | R. T. | 24 | 0 |
3 | Me | Ph | Ph | Br | NH4OH/H2O | - | NaSH | R. T. | 24 | 0 |
4 | Me | Me | Me | Br | NH4OH/H2O | MeOH | NaSH | R. T. | 24 | 0 |
5 | Me | Me | Me | Br | NH4OH/H2O | Acetone | NaSH | R. T. | 24 | 0 |
6 | Me | Me | Me | Br | NH4OH/H2O | CH2Cl2 | NaSH | R. T. | 24 | 0 |
7 | Me | Me | Me | Br | NH4OH/H2O | THF | NaSH | R. T. | 24 | 0 |
8 | Me | Me | Me | Br | NH4OH/H2O | MeOH | NaSH | Reflux | 24 | 0 |
9 | Ph | Me | Me | Br | NH4OH/H2O | MeOH | NaSH | Reflux | 24 | 0 |
10 | Me | Ph | Ph | Br | NH4OH/H2O | MeOH | NaSH | Reflux | 24 | 0 |
11 | Ph | Me | Me | Br | NH4OAc | Acetone | NaSH | R. T. | 48 | 0 |
12 | Me | Me | Me | Br | NH4OAc | Acetone | NaSH | R. T. | 48 | 0 |
13 | Me | Me | Me | Br | NH4OAc | MeOH | NaSH | R. T. | 48 | 0 |
14 | Ph | Me | Me | Br | NH4OAc | MeOH | NaSH | R. T. | 48 | 0 |
15 | Ph | Me | Me | Br | NH4OAc | MeOH | NaSH | Reflux | 24 | 0 |
16 | Me | Ph | Ph | Br | NH4OAc | AcOH | NaSH | 100 | 24 | 0 |
17 | Me | Ph | Ph | Br | NH4OAc | DMF | NaSH | 100 | 24 | 0 |
18 | Me | Ph | Ph | Br | NH4OAc | Toluene | NaSH | 100 | 24 | 0 |
19 | Me | 4-ClC6H4 | H | Br | NH4OH/H2O | - | NaSH | R. T. | 24 | 8 |
20 | Me | 4-ClC6H4 | H | Br | NH4OH/H2O | MeOH | NaSH | R. T. | 24 | 12 |
21 | Me | 4-ClC6H4 | H | Br | NH4OH/H2O | MeOH | NaSH | R. T. | 24 | <5 |
22 | Me | 4-ClC6H4 | H | Br | NH3/MeOH | MeOH | NaSH | R. T. | 24 | 20 |
23 | Me | 4-ClC6H4 | H | Br | NH3/MeOH | MeOH | NaSH, MgSO4 | R. T. | 24 | 35 |
24 | Me | 4-ClC6H4 | H | SH | NH3/MeOH | MeOH | MgSO4 | R. T. | 24 | 64 |
25 | Me | cyclohexanone | SH | NH3/MeOH | MeOH | MgSO4 | R. T. | 24 | 68 |
Compound | R1 | R2 | %Yield at R.T. | %Yield under MW |
---|---|---|---|---|
1 | 4-ClC6H4 | H | 64 | 71 |
2 | 2-ClC6H4 | H | 77 | 47 |
3 | Ph | H | 33 | 50 |
4 | 4-OHC6H4 | H | 55 | 65 |
5 | 4-CH3C6H4 | H | 69 | 49 |
6 | 2,3-(OCH3)2C6H3 | H | 69 | 75 |
7 | (3-OCH3-4-OH)C6H3 | H | 90 | 70 |
8 | (2-OCH2C≡CH)C6H4 | H | 88 | 73 |
9 | cyclohexanone | 68 | 75 |
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Gordillo-Cruz, R.E.; Gonzalez-Reyes, L.; Coporo-Reyes, M.; Zavala-Segovia, N.; Frontana-Uribe, B.A.; García-Eleno, M.A.; Unnamatla, M.V.B.; Cuevas-Yañez, E. Microwave-Assisted Asinger Synthesis of Thiazolines. Chem. Proc. 2021, 3, 27. https://doi.org/10.3390/ecsoc-24-08316
Gordillo-Cruz RE, Gonzalez-Reyes L, Coporo-Reyes M, Zavala-Segovia N, Frontana-Uribe BA, García-Eleno MA, Unnamatla MVB, Cuevas-Yañez E. Microwave-Assisted Asinger Synthesis of Thiazolines. Chemistry Proceedings. 2021; 3(1):27. https://doi.org/10.3390/ecsoc-24-08316
Chicago/Turabian StyleGordillo-Cruz, Raúl Eduardo, Liliana Gonzalez-Reyes, Milton Coporo-Reyes, Nieves Zavala-Segovia, Bernardo A. Frontana-Uribe, Marco A. García-Eleno, M. V. Basavanag Unnamatla, and Erick Cuevas-Yañez. 2021. "Microwave-Assisted Asinger Synthesis of Thiazolines" Chemistry Proceedings 3, no. 1: 27. https://doi.org/10.3390/ecsoc-24-08316