Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)
Abstract
:1. Introduction
2. Materials and Methods
2.1. General
2.2. General Procedure for the Synthesis of 2-Hydroxynaphthalen-1-yl-carbamates (4a–i)
2.3. Ring-Closing Reaction from methyl ((2-hydroxynaphthalen-1-yl)(phenyl)methyl)carbamate (4d) to naphta[1,2]oxazinone Derivatives (5d)
2.4. General Procedure for the Synthesis of naphta[1,2]oxazinones (5a–f)
3. Results and Discussion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry | 1/2/3a | T3P® (equiv.) | Time (h) | Solvent | Temperature (°C) | Yield (%) |
---|---|---|---|---|---|---|
1 | 1/1/1 | 1 | 26 | EtOAc | r.t. | 32 |
2 | 1/1/1 | 1 | 2 | EtOAc | 77 | 53 |
3 | 1/1/1 | 0 | 2 | EtOAc | 77 | 0 |
4 | 1/1.1/1.1 | 1.1 | 2 | EtOAc | 77 | 83 |
5 | 1/1.3/1.3 | 1.3 | 2 | EtOAc | 77 | 83 |
6 | 1/1.1/1.1 | 1.5 | 2 | EtOAc | 77 | 81 |
7 | 1/1.1/1.1 | 5 | 5 | EtOAc | 77 | 73 |
8 | 1/1.1/1.1 | 1.1 | 2 | THF | 66 | 90 |
9 | 1/1.1/1.1 | 1.1 | 2 | MeCN | 82 | 73 |
10 | 1/1.1/1.1 | 1.1 | 2 | CHCl3 | 62 | 89 |
11 | 1/1.1/1.1 | 1.1 | 2 | MTBE | 65 | 83 |
12 | 1/1.1/1.1 | 1.1 | 2 | MeTHF | 80 | 85 |
13 | 1/1.1/1.1 | 1.1 | 2 | PhMe | 80 | 91 |
14 | 1/1.1/1.1 | 1.1 | 0.5 | PhMe | 80 | 89 |
Entry | T3P® (equiv.) | Temperature (°C) | Reaction Time | Yield (%) |
---|---|---|---|---|
1 | - | 80 | 26 h | n.r. a |
2 | 1.1 | 80 | 30 min | 0 b |
3 | 1.1 | 135 | 4 h | 0 b |
4 | 2 | 135 | 70 min | 0 b |
5 | 2 | 160 | 60 min | 75 |
6 | 1.1 | 160 | 90 min | 47 |
7 | 3 | 160 | 45 min | 50 |
8 | 2 | 135 c | 90 min | 18 |
9 | 2 | 160 c | 30 min | 36 |
Method | Number of Steps | Reaction Time (min) | Temperature (°C) | T3P® (equiv.) | Yield (%) | ||||
---|---|---|---|---|---|---|---|---|---|
MW/∆ | 1 or 2 | Step1 | Step2 | Step1 | Step2 | Step1 | Step2 | ||
A | ∆ | 1 | 90 | - | 160 | - | 3.1 | - | 26 |
B | ∆ | 2 | 30 | 90 | 80 | 160 | 3.1 | - | 28 |
C | ∆ | 2 | 30 | 90 | 80 | 160 | 1.1 | 2.0 | 51 |
D | MW | 1 | 55 | - | 160 | - | 3.1 | - | 38 |
E | MW | 2 | 15 | 35 | 80 | 160 | 3.1 | - | 52 |
F | MW | 2 | 15 | 35 | 80 | 160 | 1.1 | 2.0 | 45 |
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Varga, V.; Ábrányi-Balogh, P.; Milen, M. Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®). Chemistry 2020, 2, 600-612. https://doi.org/10.3390/chemistry2020037
Varga V, Ábrányi-Balogh P, Milen M. Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®). Chemistry. 2020; 2(2):600-612. https://doi.org/10.3390/chemistry2020037
Chicago/Turabian StyleVarga, Valentina, Péter Ábrányi-Balogh, and Mátyás Milen. 2020. "Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)" Chemistry 2, no. 2: 600-612. https://doi.org/10.3390/chemistry2020037