After consulting a lot of data, we found that this compound(20198-19-0)Recommanded Product: 2-Aminoquinazolin-4(3H)-one can be used in many types of reactions. And in most cases, this compound has more advantages.
The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Condensations of isatinic acid with ureas, ethyl carbamate, and guanidine》. Authors are Stefanovic, Gj.; Lorenc, L. J.; Mihailovic, M. Lj..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Recommanded Product: 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.
The title condensations gave high yields of 2-derivatives of quinazoline-4-carboxylic acid o-C6H4.N:CR’.N:CCO2R. KOH solution (20% aqueous) containing 0.1 mole KOH added to 14.7 g. isatin (II), the mixture warmed at 40° until yellow, the solution evaporated to dryness in vacuo below 40°, and the residue crystallized from EtOH gave K isatinate (III). Heating 4.06 g. III with 6.0 g. urea at 130-40° 10 hrs., treating the mixture with hot EtOH, and cooling gave 3.84 g. I(R = K, R’ = OH) (IV), which with aqueous AgNO3 was converted to I (R = Ag, R’ = OH) (V). V (2.97 g.) refluxed 6 hrs. with 2.13 g. MeI in 20 ml. anhydrous Et2O, the mixture filtered, the AgI washed with hot EtOH, the filtrate and washings combined, and evaporated to dryness in vacuo gave 2.18 g. crude I (R = Me, R’ = OH) (VI), m. 200-1° (EtOH). When anhydrous MeOH was used for washing and crystallization, VI crystallized with 1 mol. MeOH, m. 216°. IV (9.1 g.) in 90 ml. H2O treated at 5° with an equivalent amount of 8% aqueous HCl, the precipitate filtered off, and washed with cold H2O gave 7.5 g. I (R = H, R’ = OH) (VII).H2O, m. 264-5°, pK 3.10 (H2O-EtOH), which gave the anhydrous acid (VIII) on prolonged drying over P2O5 in vacuo. This (2.08 g.) treated dropwise with excess CH2N2 in anhydrous Et2O at ice-bath temperature gave, after evaporation of solvent, crude I (R = Me, R’ = OMe) (IX), m. 99-100° (EtOH). IX (240 mg.) refluxed 30 min. with 12 ml. 0.1N aqueous NaOH, the solution cooled to 5°, acidified with 5% aqueous HCl to Congo red, and filtered gave 190 mg. I (R = H, R’ = OMe) (X), m. 156° (purification through the Na salt). X (102 mg.) heated at 160° to cessation of CO2 evolution and the product sublimed at 10-15 mm. gave 48.2 mg. 2-methoxyquinazoline, m. 56°. Boiling 7.50 g. VIII in 75 ml. H2O 6 hrs., cooling, and filtering gave 5.0 g. crude 2-quinazolone (XI), converted to the hydrochloride, m. above 300°, by boiling concentrated HCl and addition of EtOH. This gave pure XI, m. 282-4°, with boiling EtOH. III (10.15 g.) heated with (H2N)2C:NH 4 hrs. at 125°, followed by dissolution with H2O, filtration, and acidification of the filtrate with 5% aqueous HCl to Congo red gave 8.9 g. I (R = H, R’ = NH2) (XII), which, after solution in NaHCO3 and precipitation with 5% sq. HCl, gave pure XII, m. 210°. Treating XII at 5° in Et2O with a slight excess of ethereal CH2N2, evaporating the solvent, and crystallizing the crude product from EtOH gave I (R = Me, R’ = NH2) (XIII), m. 144-5°. XII (100 mg.) decarboxylated at 220-5°/10-15 mm. yielded 63 mg. 2-aminoquinazolone, m. 205°, which sublimed during the decarboxylation. IV was also obtained in high yield by reaction of PhNHCONH2, Me2NCONH2, or NH2CO2Et with III. A discussion of lactim-lactam tautomerization was given, based on the methylation reactions and infrared spectra.
After consulting a lot of data, we found that this compound(20198-19-0)Recommanded Product: 2-Aminoquinazolin-4(3H)-one can be used in many types of reactions. And in most cases, this compound has more advantages.
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