An Unexpected Reaction of Isodehydracetic Acid with Amines in the Presence of 1-Ethyl-3-(3-dimethylaminopropyl) Carbodiimide Hydrochloride Yields a New Type of β-Enaminones
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Procedures
3.1. General Information
3.2. Synthesis of Isodehydracetic Acid
3.3. General Procedure for Synthesis of Compounds 2, 3 and 4a–4w
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
Abbreviations
DCC | N,N′-Dicyclohexylcarbodiimide |
DMAP | 4-Dimethylaminopyridine |
EDC | 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride |
HOBT | Hydroxybenzotriazole |
HATU | 2-(7-Azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate |
DIPEA | N,N-Diisopropylethylamine |
DMF | N,N-Dimethylformamide |
DCM | Dichloromethane |
THF | Tetrahydrofuran |
Appendix A
References
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Sample Availability: Samples of the compounds are available from the authors. |
Entry | Condition | Yield of 1 (%) a |
---|---|---|
1 | DCC (1.3 equiv.)/DMAP (0.1 equiv.), dry DCM, r.t., 6 h | 15 |
2 | EDC (1.3 equiv.)/HOBT (1.3 equiv.), DCM, r.t., 6 h | 61 |
3 | HATU (1.3 equiv.)/DIPEA (3.0 equiv.), dry DCM, r.t., 6 h | 36 |
4 | EDC (1.3 equiv.), DCM, r.t., 2 h | 66 |
5 | EDC (1.3 equiv.), DCM, r.t., 30 min | 62 |
6 | EDC (3 equiv.), DCM, r.t., 30 min | 65 |
7 | EDC (1.3 equiv.), DMF, r.t., 30 min | 34 |
8 | EDC (3 equiv.), DCM, reflux, 30 min | n.d. b |
9 | Et3N (or DIPEA, DBU), 0 ℃ to reflux | n.d. c |
10 | i) SOCl2; ii) Et3N, THF, 0 ℃ to r.t. | n.d. b |
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Wang, D.; Shi, H. An Unexpected Reaction of Isodehydracetic Acid with Amines in the Presence of 1-Ethyl-3-(3-dimethylaminopropyl) Carbodiimide Hydrochloride Yields a New Type of β-Enaminones. Molecules 2020, 25, 2131. https://doi.org/10.3390/molecules25092131
Wang D, Shi H. An Unexpected Reaction of Isodehydracetic Acid with Amines in the Presence of 1-Ethyl-3-(3-dimethylaminopropyl) Carbodiimide Hydrochloride Yields a New Type of β-Enaminones. Molecules. 2020; 25(9):2131. https://doi.org/10.3390/molecules25092131
Chicago/Turabian StyleWang, Delong, and Hui Shi. 2020. "An Unexpected Reaction of Isodehydracetic Acid with Amines in the Presence of 1-Ethyl-3-(3-dimethylaminopropyl) Carbodiimide Hydrochloride Yields a New Type of β-Enaminones" Molecules 25, no. 9: 2131. https://doi.org/10.3390/molecules25092131