Synthesis of Polysubstituted 1,2-Dihydro-3H-pyrrolo[1,2-a]indol-3-ones through Domino Palladium-Catalyzed Reactions of Indol-2-ylmethyl Acetates with 1,3-Dicarbonyl Derivatives
Abstract
:1. Introduction
2. Results and Discussions
3. Materials and Methods
3.1. General Information
3.2. Synthetic Procedures and Characterization Data
3.2.1. General Procedure for the Preparation of (1H-indol-2-yl)methyl Acetates
3.2.2. Characterization Data of (1H-indol-2-yl)methyl Acetates (1a, c-h; 4a-b)
3.2.3. General Procedure for the Preparation of 5-(aryl-2-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-diones (2)
3.2.4. Characterization Data of 5-(aryl-2-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-diones (2)
3.2.5. Typical Procedure for the Preparation of 1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-ones (3a-m; 5a-d): Synthesis of 2-methyl-1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-one (3a)
3.2.6. Characterization Data of of 1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-ones (3b-3m; 5a-d)
3.2.7. Typical Procedure for the Preparation of 1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-one (8), ethyl 3-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate (11) and 2-acetyl-1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-one (13)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | 1 | Catalyst | Base | Solvent | T (°C) | t (h) | Yield 3a (%) b |
---|---|---|---|---|---|---|---|
1 | 1a | / | K2CO3 | DMSO | 100 | 7 | 55 |
2 | 1b | / | NaH | DMSO | 100 | 72 | 42(17) c |
3 | 1b | Pd2(dba)3/PPh3 | K2CO3 | MeCN | 70 | 5.5 | 68 |
4 | 1b | Pd2(dba)3/PPh3 | K2CO3 | MeCN | 80 | 7 | 68 |
5 | 1b | Pd2(dba)3/PPh3 | K2CO3 | DMSO | 80 | 1.5 | 75 |
6 | 1b | Pd2(dba)3/P(2-furyl)3 | K2CO3 | DMSO | 80 | 1 | 78 |
7 | 1b | Pd2(dba)3/dppf | K2CO3 | DMSO | 80 | 1.5 | 85 |
8 | 1b | Pd2(dba)3/dppf | / | DMSO | 80 | 24 | (30) c |
9 | 1a | Pd2(dba)3/PPh3 | K2CO3 | MeCN | 100 | 40 | 67 |
10 | 1a | Pd2(dba)3/PPh3 | K2CO3 | DMSO | 100 | 5.5 | 75 |
11 | 1a | Pd2(dba)3/dppf | K2CO3 | DMSO | 100 | 2 | 88 |
12 | 1a | Pd2(dba)3/dppf | K2CO3 | DMSO | 100 | 2 | /(/) c,d |
Entry | 1 | R1 | R2 | 2 | R3 | t (h) | Yield 3 (%) b |
---|---|---|---|---|---|---|---|
1 | 1a | H | H | 2b | -CH2(4-OMe-C6H4) | 1 | 3b (78) |
2 | 1a | H | H | 2c | -CH2(furyl) | 4 | 3c (63) |
3 | 1a | H | H | 2d | -Ph | 24 | (/) |
4 | 1a | H | H | 2e | -CH2CH2CO2Me | 3 | 3d (74) |
5 | 1c | 5-Me | H | 2a | -Me | 3 | 3e (70) |
6 | 1d | 5-Br | H | 2a | -Me | 5 | 3f (50) |
7 | 1e | 5-(4-Me-C6H4) | H | 2a | -Me | 4.5 | 3g (70) |
8 | 1f | 5-(4-F,3-Me-C6H3) | H | 2a | -Me | 5 | 3h (70) |
9 | 1g | H | Ph | 2a | -Me | 3 | 3i (58) |
10 | 1g | H | -Ph | 2b | -CH2(4-OMe-C6H4) | 2 | 3j (64) |
11 | 1g | H | -Ph | 2c | -CH2(2-furyl) | 2 | 3k (54) |
12 | 1g | H | -Ph | 2e | -CH2CH2CO2Me | 2.5 | 3l (66) |
13 | 1h | H | 4-CF3-C6H4 | 2a | -Me | 1 | 3m (71) |
14 | H | H | 2a | -Me | 3 | 3a (72) c |
Entry | 4 | R1 | 2 | R2 | t (h) | Ratio 5/5′ b | Yield 5 + 5′ (%) c |
---|---|---|---|---|---|---|---|
1 | 4a | -Ph | 2a | -Me | 2 | 84/16 | 5a + 5′a (74) |
2 | 4a | -Ph | 2b | -CH2(4-OMe-C6H4) | 3 | 94/6 | 5b + 5′b (50) |
3 | 4a | -Ph | 2c | -CH2(furyl) | 2 | 74/26 | 5c + 5′c (52) |
4 | 4b | -Me | 2a | -Me | 24 | 84/16 | 5d + 5′d (76) |
Entry | 14 | R1 | R2 | t (h) | Yield 3 (%) | Yield 15 (%) b |
---|---|---|---|---|---|---|
1 | 14a | -Me | -Me | 1 | 3a (45) | 15a (18) c |
2 | 14a | -Me | -Me | 3 | 3a (46) | traces |
3 | 14b | -OEt | -Me | 24 | / | 15b (60) |
4 | 14c | -Me | -CH2CH = CH | 4 | 3n (71) | / |
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Iazzetti, A.; Arcadi, A.; Dessalvi, S.; Fabrizi, G.; Goggiamani, A.; Marrone, F.; Serraiocco, A.; Sferrazza, A.; Ullah, K. Synthesis of Polysubstituted 1,2-Dihydro-3H-pyrrolo[1,2-a]indol-3-ones through Domino Palladium-Catalyzed Reactions of Indol-2-ylmethyl Acetates with 1,3-Dicarbonyl Derivatives. Catalysts 2022, 12, 1516. https://doi.org/10.3390/catal12121516
Iazzetti A, Arcadi A, Dessalvi S, Fabrizi G, Goggiamani A, Marrone F, Serraiocco A, Sferrazza A, Ullah K. Synthesis of Polysubstituted 1,2-Dihydro-3H-pyrrolo[1,2-a]indol-3-ones through Domino Palladium-Catalyzed Reactions of Indol-2-ylmethyl Acetates with 1,3-Dicarbonyl Derivatives. Catalysts. 2022; 12(12):1516. https://doi.org/10.3390/catal12121516
Chicago/Turabian StyleIazzetti, Antonia, Antonio Arcadi, Stefano Dessalvi, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Andrea Serraiocco, Alessio Sferrazza, and Karim Ullah. 2022. "Synthesis of Polysubstituted 1,2-Dihydro-3H-pyrrolo[1,2-a]indol-3-ones through Domino Palladium-Catalyzed Reactions of Indol-2-ylmethyl Acetates with 1,3-Dicarbonyl Derivatives" Catalysts 12, no. 12: 1516. https://doi.org/10.3390/catal12121516