Ru(II)-Catalyzed C–H Activation Reaction between 2-Phenyl­quinazolinone and Vinylene Carbonate

Yuncan Chen; Xin Huang; Yingying Xu; Jianglian Li; Ruizhi Lai; Mei Guan; Yong Wu

doi:10.1055/a-1608-5381

Synlett, Table of Contents

Synlett 2021; 32(19): 1963-1968
DOI: 10.1055/a-1608-5381

letter

Ru(II)-Catalyzed C–H Activation Reaction between 2-Phenylquinazolinone and Vinylene Carbonate

Authors

Yuncan Chen

^aWest China Hospital, Sichuan University, No. 37 Guoxue Lane, Chengdu, Sichuan 610041, P. R. of China

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
Xin Huang

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
Yingying Xu

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
Jianglian Li

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
Ruizhi Lai

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China
Mei Guan∗

^aWest China Hospital, Sichuan University, No. 37 Guoxue Lane, Chengdu, Sichuan 610041, P. R. of China
Yong Wu∗

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China

Abstract

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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.

Key words

C–H activation - ruthenium - annulation reaction - vinylene carbonate - quinazolinones

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References

References and Notes

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25 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.
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.

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Ru(II)-Catalyzed C–H Activation Reaction between 2-Phenyl­quinazolinone and Vinylene Carbonate

Authors

Ru(II)-Catalyzed C–H Activation Reaction between 2-Phenylquinazolinone and Vinylene Carbonate