Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives

Abstract

We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.

Key words

copper catalysis - tandem reactions - aminobenzamides - tertiary amines - quinazolinones

• References

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• 19 2-Methyl-3-phenylquinazolin-4(3H)-one (3); Typical Procedure A reaction tube was charged under air with 2-aminobenzanilide (1a, 0.2 mmol), Et₃N (2a, 0.6 mmol), Cu₂O (10 mol%), PCy₃ (10 mol%), and CHCl₃ (2 mL). The vessel was sealed, heated at 100 °C (oil-bath temperature) for 24 h, and then cooled to r.t. DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1 h. After filtration of the mixture and evaporation of the solvent under reduced pressure, the crude product was purified by column chromatography [silica gel, hexane–EtOAc (3:1)] to give a light-yellow solid; yield: 42.0 mg (89%); mp 147–148 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.27 (dd, J = 8.0, 1.0 Hz, 1 H), 7.79–7.76 (m, 1 H), 7.69 (d, J = 8.0 Hz, 1 H), 7.58–7.55 (m, 2 H), 7.53–7.51 (m, 1 H), 7.49–7.46 (m, 1 H), 7.28–7.26 (m, 2 H), 2.26 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 162.2, 154.3, 147.4, 137.7, 134.6, 130.0, 129.3, 128.0, 127.1, 126.7, 126.7, 120.8, 24.3. LRMS (EI, 70 eV): m/z (%) = 236 (100), 235 (80), 221 (58), 143 (16), 77 (50).