Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions †
Abstract
:1. Introduction
2. Results
3. Conclusions
4. Materials and Methods
4.1. General Methods
4.2. General Procedure
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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No. | Solvent | Base (equiv.) | X | Y | 2 or 3 (equiv) | 1a (equiv.) | Yield of 4a | Yield of 5a |
---|---|---|---|---|---|---|---|---|
1 | THF | DABCO (1.2) | COOH | COOH | 1.0 | 1.0 | 69 | 23 |
2 | THF | DMAP (1.2) | COOH | COOH | 1.0 | 1.0 | 62 | 50 |
3 | THF | Pyrrolidine (1.2) | COOH | COOH | 1.0 | 1.0 | 65 | 50 |
4 | THF | 2,6-lutidine (1.2) | COOH | COOH | 1.0 | 1.0 | 54 | 38 |
5 | THF | TEA (1.2) | COOH | COOH | 1.0 | 1.0 | 71 | 21 |
6 | THF | DIPEA (1.2) | COOH | COOH | 1.0 | 1.0 | 74 | 42 |
7 | THF | NMM (1.2) | COOH | COOH | 1.0 | 1.0 | 77 | 56 |
8 | THF | NMM (1.2) | COOH | COOH | 1.5 | 1.0 | 71 | 63 |
9 | THF | NMM (1.2) | COOH | COOH | 1.2 | 1.0 | 47 | 52 |
10 | THF | NMM (1.4) | COOH | COOH | 1.0 | 1.2 | 82 | 61 |
11 | THF | NMM (1.7) | COOH | COOH | 1.0 | 1.5 | 98 | 70 |
12 | THF | NMM (2.2) | COOH | COOH | 1.0 | 2.0 | 92 | 70 |
13 | Toluene | NMM (1.7) | COOH | COOH | 1.0 | 1.5 | 19 | 40 |
14 | MeCN | NMM (1.7) | COOH | COOH | 1.0 | 1.5 | 75 | 69 |
15 | CH2Cl2 | NMM (1.7) | COOH | COOH | 1.0 | 1.5 | 75 | 54 |
16 | THF | NMM (1.7) | COOH | H | 2b (1.0) | 1.5 | no reaction | - |
17 | THF | NMM (1.7) | COOH | H | 3b (1.0) | 1.5 | - | no reaction |
18 | THF | NMM (0.2) | H | COOH | 2a (1.0) | 1b (1.5) | no reaction | - |
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Bojanowski, J.; Albrecht, A. Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions. Molecules 2021, 26, 4689. https://doi.org/10.3390/molecules26154689
Bojanowski J, Albrecht A. Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions. Molecules. 2021; 26(15):4689. https://doi.org/10.3390/molecules26154689
Chicago/Turabian StyleBojanowski, Jan, and Anna Albrecht. 2021. "Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions" Molecules 26, no. 15: 4689. https://doi.org/10.3390/molecules26154689