One-Pot Chemoenzymatic Multicomponent Synthesis of Thiazole Derivatives
Abstract
:1. Introduction
2. Results and Discussion
Entry | Catalyst | Time (h) | Yield (%) b |
---|---|---|---|
1 | Trypsin from porcine pancreas (PPT) | 7 | 90 |
2 | α-Amylase from hog pancreas | 7 | 60 |
3 | Diastase from Aspergillus oryzae | 7 | 67 |
4 | α-Amylase from Aspergillus oryzae | 7 | 53 |
5 | Lipase AT30 | 7 | 61 |
6 | Amano lipase M from Mucor javanicus | 7 | 40 |
7 | Lipase from porcine pancreas | 7 | 63 |
8 | Bovine serum albumin (BSA) | 7 | 50 |
9 | Blank (no enzyme) | 7 | Trace |
10 | Denatured typsin from porcine pancreas c | 7 | Trace |
Entry | Solvent | T/°C | Yield (%) b |
---|---|---|---|
1 | Ethanol | 45 | 90 |
2 | CH2Cl2 | 45 | 75 |
3 | n-Hexane | 45 | 33 |
4 | CH3CN | 45 | 32 |
5 | Methanol | 45 | 31 |
6 | Acetone | 45 | 10 |
7 | 1,4-Dioxane | 45 | Trace |
8 | THF | 45 | Trace |
9 | Water | 45 | Trace |
Entry | PPT amount (mg) | Temp (°C) | Time (h) | Yield (%) b |
---|---|---|---|---|
1 | 20 | 20 | 7 | 46 |
2 | 20 | 30 | 7 | 59 |
3 | 20 | 35 | 7 | 73 |
4 | 20 | 40 | 7 | 80 |
5 | 20 | 45 | 7 | 90 |
6 | 20 | 50 | 7 | 85 |
7 | 20 | 55 | 7 | 82 |
8 | 10 | 45 | 7 | 70 |
9 | 20 | 45 | 7 | 88 |
10 | 30 | 45 | 7 | 80 |
11 | 40 | 45 | 7 | 77 |
12 | 50 | 45 | 7 | 71 |
13 | 20 | 45 | 6 | 75 |
14 | 20 | 45 | 7 | 90 |
15 | 20 | 45 | 8 | 88 |
Entry | Products | R1 | R2 | R3 | Yield (%) |
---|---|---|---|---|---|
1 | 4a | C2H5- | C2H5- | CH3- | 90 b (82) c |
2 | 4b | C2H5- | C2H5- | C2H5- | 69 (62) |
3 | 4c | CH3- | CH3- | CH3- | 93 (83) |
4 | 4d | CH3- | CH3- | C2H5- | 79 (70) |
5 | 4e | CH3- | 94 (85) | ||
6 | 4f | C2H5- | 88 (79) | ||
7 | 4g | -CH2CH2OCH2CH2- | CH3- | 80 (72) | |
8 | 4h | -CH2CH2OCH2CH2- | C2H5- | 63 (52) | |
9 | 4i | -CH2CH2CH2CH2- | CH3- | 85 (73) | |
10 | 4j | -CH2CH2CH2CH2- | C2H5- | 74 (61) | |
11 | 4k | H | CH3- | (75) |
3. Experimental
3.1. General
3.2. General Procedure for the Synthesis of Thiazole Derivatives
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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- Sample Availability: Samples of the compounds are available from the authors.
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Zheng, H.; Mei, Y.-J.; Du, K.; Cao, X.-T.; Zhang, P.-F. One-Pot Chemoenzymatic Multicomponent Synthesis of Thiazole Derivatives. Molecules 2013, 18, 13425-13433. https://doi.org/10.3390/molecules181113425
Zheng H, Mei Y-J, Du K, Cao X-T, Zhang P-F. One-Pot Chemoenzymatic Multicomponent Synthesis of Thiazole Derivatives. Molecules. 2013; 18(11):13425-13433. https://doi.org/10.3390/molecules181113425
Chicago/Turabian StyleZheng, Hui, Yi-Jia Mei, Kui Du, Xian-Ting Cao, and Peng-Fei Zhang. 2013. "One-Pot Chemoenzymatic Multicomponent Synthesis of Thiazole Derivatives" Molecules 18, no. 11: 13425-13433. https://doi.org/10.3390/molecules181113425