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Synlett 2021; 32(19): 1963-1968
DOI: 10.1055/a-1608-5381
DOI: 10.1055/a-1608-5381
letter
Ru(II)-Catalyzed C–H Activation Reaction between 2-Phenylquinazolinone and Vinylene Carbonate
We are grateful for the support from the National Natural Science Foundation of China (NSFC; 81602954, 81573286, 81373259, and 81773577).
Abstract
In the report, we described the ruthenium(II)-catalyzed C–H activation/cyclization of 2-arylquinazolinones with vinyl carbonate for the synthesis of different fused quinazolinones. Through this strategy, the 6-hydroxy-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-one and 8H-isoquino[1,2-b] quinazolin-8-one have been obtained, respectively, under different temperatures. Additionally, the reaction features broad substrate scope and good yields, only producing carbon dioxide as byproduct. Moreover, we performed preliminary mechanistic studies of this reaction and proposed a possible mechanism.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1608-5381.
- Supporting Information
Publication History
Received: 14 July 2021
Accepted after revision: 24 August 2021
Accepted Manuscript online:
24 August 2021
Article published online:
18 October 2021
© 2021. Thieme. All rights reserved
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Wang L.-L,
Zhang S.-B.
CN112125900A, 2020
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General Procedure for the Preparation of Compounds 3
2-Phenylquinazolin-4(3H)-one (1, 0.15 mmol), vinylene carbonate (2a, 0.3 mmol), [Ru(p-cymene)Cl2]2 (5 mol%), AgOTf (20 mol%), and Ag2SO4 (20 mol%) were added to a Schlenk tube equipped with a stir bar. DCE (1.5 mL) was added, and the mixture was stirred at 110 °C for 24 h under argon atmosphere. After completion, the solvent was evaporated under reduced pressure and the remaining residue was purified by flash column chromatography on silica gel with EtOAc/petroleum ether.
3-Methyl-8H-isoquinolino[1,2-b]quinazolin-8-one (3ba)
Yield 88% (34.32 mg); white solid; mp 186.2–188.1 °C. 1H NMR (400 MHz, CDCl3): δ = 8.90 (d, J = 8.3 Hz, 1 H), 8.59 (d, J = 7.8 Hz, 1 H), 8.43 (d, J = 7.8 Hz, 1 H), 7.86–7.80 (m, 2 H), 7.47 (ddd, J = 8.2, 6.3, 1.9 Hz, 1 H), 7.43 (d, J = 8.3 Hz, 1 H), 7.36 (s, 1 H), 6.93 (d, J = 7.8 Hz, 1 H), 2.50 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 159.4, 147.6, 146.2, 142.8, 134.7, 132.9, 129.9, 127.3, 127.2, 127.1, 126.3, 125.4, 124.9, 121.8, 117.5, 113.1, 21.7. HRMS (ESI): m/z calcd for C17H12N2OH+: 261.1022; found: 261.1023.
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26
General Procedure for the Preparation of Compounds 4
2-Phenylquinazolin-4(3H)-one (1, 0.15 mmol), vinylene carbonate (2a, 0.3 mmol), [Ru(p-cymene)Cl2]2 (5 mol%), and AgNTf2 (20 mol%) were added to a Schlenk tube equipped with a stir bar. DCE (1.5 mL) was added, and the mixture was stirred at 50 °C for 24 h under argon atmosphere. After completion, the solvent was evaporated under reduced pressure and the remaining residue was purified by flash column chromatography on silica gel with EtOAc/petroleum ether.
6-Hydroxy-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-one (4aa)
Yield 97% (38.4 mg); white solid; mp > 200 °C. 1H NMR (400 MHz, DMSO-d
6): δ = 8.41 (dd, J = 7.9, 1.3 Hz, 1 H ), 8.20 (dd, J = 8.0, 1.5 Hz, 1 H), 7.86 (ddd, J = 8.5, 7.1, 1.6 Hz, 1 H), 7.75 (d, J = 8.1 Hz, 1 H), 7.54 (m, 2 H), 7.45 (t, J = 7.5 Hz, 1 H), 7.41 (d, J = 7.5 Hz, 1 H), 6.73 (d, J = 4.3 Hz, 1 H), 6.67 (td, J = 3.9, 2.0 Hz, 1 H), 3.31 (d, J = 3.5 Hz, 1 H), 3.18 (dd, J = 16.4, 2.1 Hz, 1 H). 13C NMR (101 MHz, DMSO-d
6): δ = 160.7, 148.6, 147.8, 135.2, 135.1, 132.3, 129.5, 128.8, 127.8, 127.4, 127.3, 127.1, 126.9, 121.1, 71.5, 34.8. HRMS (ESI): m/z calcd for C16H12N2O2H+: 265.0972; found: 265.0971.