Copper(I) Iodide Promoted [3+2]-Cycloaddition/Oxidation to Construct Pyrrolo[2,1-a]isoquinolinoquinones from Naphthoquinones and Tetrahydroisoquinolines

Abstract

A copper-catalyzed, three-component, one-pot, 1,3-dipole cycloaddition/oxidation has been developed to construct pyrrolo[2,1-a]isoquinolinoquinone derivatives, with environmentally friendly oxygen as the oxidant. The pyrrolo[2,1-a]isoquinolinoquinone products were obtained from naturally available tetrahydroisoquinolines, 1,4-naphthoquinones, and benzaldehydes in medium yields.

Key words

pyrroloisoquinolinoquinones - copper catalysis - tetrahydroisoquinolines - [3+2]-cycloaddition - oxidation - multicomponent reaction

Publication History

Received: 10 December 2021

Accepted after revision: 03 January 2022

Accepted Manuscript online:
03 January 2022

Article published online:
10 February 2022

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• 25 8-Phenyl-5,6-dihydrobenzo[5,6]isoindolo[1,2-a]isoquinoline-9,14-dione (4a); Typical Procedure A mixture of 1,2,3,4-tetrahydroisoquinoline (1a; 0.6 mmol, 0.0799 g), PhCHO (2a; 0.6 mmol, 0.0637 g), 4 Å MS (~0.2 g), CuI (0.5 mmol, 0.0952 g), and BzOH (0.1 mmol, 0.0122 g) in DCE (2.0 mL) was stirred in a 25 mL reaction tube at 50 °C for 2–3 h under O₂ (balloon). 1,4-Naphthoquinone (3a; 0.5 mmol, 0.0791 g) was then added, and the reaction was continued for 24 h. When the reaction was complete (TLC), the mixture was poured into H₂O (50 mL) and extracted with CH₂Cl₂ (3 × 50 mL). The combined organic layer was dried (MgSO₄), and the solvent was removed with a rotary evaporator. Purification of the crude product by column chromatography [silica gel, CH₂Cl₂–PE (1:1)] gave a yellow solid; yield: 0.1378 g (73%); mp 240–242 °C. ¹H NMR (500 MHz, CDCl₃): δ = 9.09 (d, J = 7.8 Hz, 1 H), 8.30 (dd, J = 7.6, 1.1 Hz, 1 H), 8.13 (dd, J = 7.5, 1.2 Hz, 1 H), 7.64 (m, 2 H), 7.54–7.47 (m, 5 H), 7.44 (t, J = 7.4 Hz, 1 H), 7.33 (m, 1 H), 7.22 (t, J = 7.0 Hz, 1 H), 3.95–3.88 (m, 2 H), 2.97 (t, J = 6.5 Hz, 2 H). ¹³C NMR (125 MHz, CDCl₃): δ = 180.14, 180.10, 137.86, 136.38, 136.24, 135.30, 134.31, 133.79, 132.91, 132.72, 130.48 (2 C), 129.52, 129.48, 128.61, 128.42 (2 C), 127.42, 127.34, 127.25, 127.11, 126.36, 119.53, 117.48, 42.29, 29.54. HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₆H₁₇NNaO₂: 398.1157; found: 398.1149.