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Synlett 2022; 33(01): 66-69
DOI: 10.1055/a-1661-3378
DOI: 10.1055/a-1661-3378
letter
One-Pot Synthesis of 3-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones by DEAD-Promoted Oxidative Ugi–Wittig Reaction Starting from Phosphonium Salt Precursors
We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (21572075) and the 111 Project (B17019).
Abstract
A new one-pot synthesis of 3-(1,2,3,4-tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones by DEAD-promoted oxidative Ugi–Wittig reaction was developed. The sequential reactions of (2-carboxybenzyl)triphenylphosphonium salts, isocyanides, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced 3-(1,2,3,4-tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones in moderate to good overall yields in the presence of DEAD and Et3N.
Key words
isoquinolin-1(2H)-one - oxidative Ugi reaction - Wittig reaction - (2-carboxybenzyl)triphenylphosphonium salt - 1,2,3,4-tetrahydroisoquinolineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1661-3378.
- Supporting Information
Publication History
Received: 08 September 2021
Accepted after revision: 04 October 2021
Accepted Manuscript online:
04 October 2021
Article published online:
27 October 2021
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- 31 Preparation of 3-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones 5: General ProcedureTo a mixture of N-aryl-1,2,3,4-tetrahydroisoquinoline 3 (1 mmol), isocyanide 2 (1 mmol), phosphonium salt 1 (1 mmol) in anhydrous CH2Cl2 (3 mL) was added dropwise of a solution of DEAD (0.191 g, 1.1 mmol) in anhydrous CH2Cl2 (2 mL) at room temperature. The resulting mixture was stirred at room temperature for 24 h, and then the solvent was removed under reduced pressure. Et3N (0.202 g, 2 mmol) with toluene (5 mL) was added to the reaction system, and the reaction mixture was stirred at 110 °C for 2 h. The solvent was evaporated under reduced pressure, and the crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 30:1 to 20:1, v/v) to give 5. Compound 5a: light yellow solid (yield 0.426 g, 82%), mp 272–273 (C. 1H NMR (600 MHz, CDCl3): δ = 8.12 (d, J = 7.2 Hz, 1 H, ArH), 7.62–7.10 (m, 15 H, ArH), 6.93 (t, J = 6.6 Hz, 1 H, ArH), 6.64 (s, 1 H, =CH), 6.23 (d, J = 14.4 Hz, 1 H, NCH2 a), 5.82 (s, 1 H, NCH), 5.22 (d, J = 13.8 Hz, 1 H, NCH2 b), 3.72–3.49 (m, 2 H, NCH2), 2.91–2.50 (m, 2 H, CH2), 2.36 (s, 3 H, CH3) ppm. 13C NMR (150 MHz, CDCl3) δ = 162.6, 148.1, 145.2, 142.9, 135.8, 135.2, 134.5, 132.9, 132.3, 129.7, 129.6, 129.3, 128.7, 128.1, 127.7, 127.2, 126.4, 126.3, 124.2, 120.9, 118.0, 111.2, 62.0, 57.3, 42.5, 24.1, 21.6 ppm. HRMS (ESI-TOF): m/z [M + Na]+ calcd for C32H28N2O3SNa: 543.1713; found: 543.1734.