In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Preparation and aminolysis of 4-hydroxyquinazoline-2-sulfonic acid, published in 1965, which mentions a compound: 20198-19-0, mainly applied to , Category: chiral-nitrogen-ligands.
A saturated solution of KMnO4 is added to a solution of 8.9 g. 2-mercapto-4-hydroxyquinazoline (I) and 28 g. KOH in 100 ml. H2O at 45°, the mixture filtered, and the filtrate cooled to 0°. AcOH is added to a pH 6.5, the whole cooled to -5°, and the precipitate filtered off, and recrystallized from 70% EtOH at 0° to give a 60% yield of K 4-hydroxyquinazoline-2-sulfonate (II) (no m.p.). II is adjusted with HCl to pH 4 and heated to 100° to yield 2,4-dihydroxyquinazoline, m. 348-50°. II (2.64 g.) in 6 ml. of 2M aqueous Me2NH heated 4 hrs. at 130° gives 1.74 g. of 2-dimethylamino-4-hydroxyquinazoline (III), m. 244-6°. III.HCl m. 275°. The following analogs (IV) of III were prepared (R, % yield, m.p., and m.p. Ac derivative given): H, 90.6, 315-16°, 278-80°; Me, 74.2, 275-6°, 194-6°; Et, 82.9, 231-2°, 120-2°; Pr, 84.5, 199-200°, 118-19°; Bu, 88.4, 187-8°, 110-12°; Ph, 89.7, 260-3°, 203-4°; CH2Ph, 92.2, 214-15°, 124-5°; C6H4OMe-p, 85.7, 271-2°, 204-5°; C6H4Me-p, 91.2, 268-70°, 206-9°; cyclohexyl, 32.0, 209-11°, 204-5°; CH2CH2OH, 96.0,249-50°, -; 1-pyrrolidyl 73.2, 223-4°, -.
This literature about this compound(20198-19-0)Category: chiral-nitrogen-ligandshas given us a lot of inspiration, and I hope that the research on this compound(2-Aminoquinazolin-4(3H)-one) can be further advanced. Maybe we can get more compounds in a similar way.
Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis