Facile Synthesis of Substituted Quinazolin‐4‐(3H)‐ones Using Low‐Valence Titanium Reagent

Abstract

A short and facile synthesis of a series of 3‐aryl quinazolin‐4‐(3H)‐ones was accomplished in good yields via the intermolecular reductive coupling reaction of N‐aryl‐2‐nitrobenzamide and triethyl orthoformate promoted by TiCl₄/Zn.

Keywords:

• Quinazolin‐4‐(3H)‐ones
• Low‐valence titanium
• Synthesis

Acknowledgments

We are grateful to the Education Committee Nature Science Foundation of Jiangsu Province and the Key Laboratory of Organic Synthesis, Suzhou University for financial support.

Notes

^aX‐ray crystallography for 3a: Empirical formula C₁₄H₁₀N₂O, F _W = 222.24, T = 297(2) K, moloclinic, space group P2(1)/c, a = 12.080(2) Å, b = 7.793(1) Å, c = 11.599(1) Å, β = 97.56(1)°, V = 1082.4(2) ų, Z = 4, D_c  = 1.364 mg/m³, λ(Mo Kα) = 0.71073 Å, μ = 0.088 mm⁻¹, F(0 0 0) = 464. 170° < θ < 25.25°, R = 0.0358, wR = 0.0851, S = 0933. Largest diff. Peak and hole: 0.130 and −0.117e Å⁻³.