A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU
Abstract
:1. Introduction
2. Results and Discussion
Entry a,b | 1 | R1 | R2 | Conditions | 2 or 3 (% yield) c | Lit. |
---|---|---|---|---|---|---|
1 | 1a | H | H | KOAc, 150 °C, 4 h | 2a (94) | |
2 | KOAc, 190 °C, 72 h | 3a (71) | ||||
3 | piperidine, 150 °C, 72 h | 2a (95) | ||||
4 | DABCO, MeCN, reflux, 20 h | 3a (17) d | ||||
5 | DBN, MeCN, reflux, 20 h | 3a (48) d | ||||
6 | DBU, MeCN, reflux, 8 h | 3a (86) | ||||
7 | DBU, MeCN, rt, 20 h | 3a (82) | [14,16] | |||
8 | 1b | 5-CH3 | H | DBU, MeCN, rt, 10 h | 3b (89) | [14] |
9 | 1c | 5-F | 4’-Cl | DBU, MeCN, rt, 30 h | 3c (82) | - |
10 | 1d | 4,6-(CH3)2 | 4’-CH3 | DBU, MeCN, rt, 20 h | 3d (53) | [14] |
Entry | 4 | Time (h) | 5 | Yield (%) | ||
---|---|---|---|---|---|---|
1 | 4a | 72 | 5a | 47 | ||
2 | 4b | 72 | 5bb | 38 | ||
3 | 4c | 72 | 5c | 48 | ||
4 | 4d | 20 | 5d | 43 | ||
5 | 4e | 40 | 5e | 39 | ||
6 | 4f | 2 | 5f | 60 | ||
7 | 4g | 20 | 5g | 48 | ||
8 | 4h | 3 | 5h | 40 | ||
9 | 4i | 5 | 5i | 44 | ||
10 | 4j | 6 | 5j | 35 | ||
11 | 4k | 2 | 5k | 50 | ||
12 | 4l | 20 | 5l | 42 |
3. Experimental
3.1. General
3.2. Typical Procedure for the Synthesis of 4-Phenyl-2H-chromen-2-one (3a)
3.3. Typical Procedure for the Synthesis of 3,6-Dimethyl-4-phenyl-2H-chromen-2-one (5d)
3.4. Typical Procedure for the Synthesis of 5,7-Dimethyl-3-phenyl-4-(4’-methylphenyl)-2H-chromen-2-one (5m)
4. Conclusions
Acknowledgments
References and Notes
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- Sample Availability: Samples are available from the authors.
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Hwang, I.-T.; Lee, S.-A.; Hwang, J.-S.; Lee, K.-I. A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU. Molecules 2011, 16, 6313-6321. https://doi.org/10.3390/molecules16086313
Hwang I-T, Lee S-A, Hwang J-S, Lee K-I. A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU. Molecules. 2011; 16(8):6313-6321. https://doi.org/10.3390/molecules16086313
Chicago/Turabian StyleHwang, In-Taek, Sun-Ah Lee, Jin-Soo Hwang, and Kee-In Lee. 2011. "A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU" Molecules 16, no. 8: 6313-6321. https://doi.org/10.3390/molecules16086313