Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

Ao Li; Bin Pan; Chao Mu; Na Wang; Yu-Long Li; Qin Ouyang

doi:10.1055/a-1345-3491

Synlett, Table of Contents

Synlett 2021; 32(07): 679-684
DOI: 10.1055/a-1345-3491

letter

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

Authors

Ao Li‡

^aCollege of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
Bin Pan‡

^bCollege of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
Chao Mu

^aCollege of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
Na Wang

^bCollege of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
Yu-Long Li∗

^aCollege of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
Qin Ouyang∗

^bCollege of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China

Abstract

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Abstract

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

Key words

photocatalysis - oxidation - porphyrins - zinc catalysis - dihydroisoquinolones

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References

References and Notes

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14 3,4-Dihydroisoquinolin-1(2H)-ones 2a–t; General Procedure The appropriate N-aryltetrahydroquinoline 1 (0.1 mM, 1 equiv), ZnTPP (0.001 mM, 1% equiv, 0.68 mg), and CsF (0.3 mM, 3 equiv, 46 mg) were added to DMF (0.1 M), and the mixture was stirred at rt and irradiated by blue LEDs under air overnight. The mixture was then extracted with CH₂Cl₂ and the extracts were washed with H₂O. The combined organic phases were dried (Na₂SO₄) and concentrated under reduced pressure, and the crude product was purified by column chromatography (silica gel, PE–EtOAc). 2-Phenyl-3,4-dihydroisoquinolin-1(2H)-one (2a) White solid; yield: 15.8 mg (71%); mp 100–101 °C. ¹H NMR (600 MHz, CDCl₃): δ = 8.16 (d, J = 7.4 Hz, 1 H), 7.47 (t, J = 7.4 Hz, 1 H), 7.40 (dq, J = 16.8, 8.0 Hz, 5 H), 7.25 (d, J = 10.5 Hz, 2 H), 4.00 (t, J = 6.4 Hz, 2 H), 4.00 (t, 3.15 (t, J = 6.4 Hz, 2 H). ¹³C NMR (150 MHz, CDCl₃): δ = 164.2, 143.1, 138.3, 132.0, 129.7, 128.9, 128.7, 127.2, 126.9, 126.2, 125.3, 49.4, 28.6. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₅H₁₃NNaO: 246.0895; found: 246.0889.

Supplementary Material

Supporting Information (PDF)