Chemoselective Synthesis of N-Arylenaminones and 3-Aroylquinolines by Synergistic Control of Temperature and Amount of Catalyst

Abstract

An efficient and practical method has been developed for the divergent synthesis of N-arylenaminones and 3-aroylquinolines from 2-aminoaryl ketones and N,N-dimethylenaminones in the presence of 4-toluenesulfonic acid through synergistic control of the temperature and amount of catalyst. Furthermore, gram-scale synthesis and synthetic applications have been evaluated. Features of this protocol include controllable results, mild conditions, good functional-group tolerance, operational simplicity, and excellent yields.

Key words

divergent synthesis - arylenaminones - aroylquinolines - dimethylenaminones

• References and Notes

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• 25 (4-Methoxyphenyl)(4-methylquinolin-3-yl)methanone; Typical Procedure 1-(2-Aminophenyl)ethanone (1a; 67.5 mg, 0.5 mmol), N,N-dimethylenaminone 2a (102.5 mg, 0.5 mmol), and p-TSA (172 mg, 1.0 mmol) were dissolved in 4:1 (v/v) H₂O–EtOH (5 mL), and the mixture was stirred at 100 °C, for 6.0 h until 2a was completely consumed. The mixture was cooled to r.t., neutralized to pH 8–9 with sat. aq Na₂CO₃, and extracted with EtOAc (2 × 30 mL). The combined organic phase was washed with H₂O (20 mL), dried (Na₂SO₄), concentrated, and purified by flash column chromatography to give a yellow solid; yield: 129 mg (93%); mp 99–101 °C; IR (KBr): 1641, 1596, 1499, 1450, 1398, 1313, 1253, 1157, 926, 797, 705, 626 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 2.58 (s, 3 H, ArCH₃), 3.81 (s, 3 H, ArOCH₃), 6.87–6.89 (m, 2 H, ArH), 7.57–7.59 (m, 1 H, ArH), 7.72–7.76 (m, 3 H, ArH), 8.04 (d, J = 8.0 Hz, 1 H, ArH), 8.09 (d, J = 8.0 Hz, 1 H, ArH), 8.73 (s, 1 H, ArH). ¹³C NMR (125 MHz, CDCl₃): δ = 15.8, 55.6, 114.8, 114.8, 124.4, 127.3, 127.7, 130.2, 130.2, 130.5, 132.4, 132.6, 132.6, 143.0, 147.9, 148.5, 164.3, 195.5. HRMS (TOF ES⁺): m/z [M + H]⁺ calcd for C₁₈H₁₆NO₂: 278.1176; found: 278.1179.
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