The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Cyclic amidines. X. 2-Aminoquinazoline derivatives》. Authors are Grout, R. J.; Partridge, M. W..The article about the compound:2-Aminoquinazolin-4(3H)-onecas:20198-19-0,SMILESS:O=C1NC(N)=NC2=C1C=CC=C2).Name: 2-Aminoquinazolin-4(3H)-one. Through the article, more information about this compound (cas:20198-19-0) is conveyed.
cf. CA 54, 3439a. 2-(Substituted amino)- and 3-substituted 2-aminoquin-azolines were produced by interaction of a urea, an arenesulfonyl chloride, and Me anthranilate (I). Rearrangements of 3-substituted 2-amino-3,4-dihydro-4-oxoquinazolines to their 2-(substituted amino)isomers, aminolyzes, alkylations, and transalkylations of quinazoline derivatives were examined None of the compounds reported was of therapeutic interest. EtNHCONH2 (8.8 g.) suspended in 30 mL. C5H5N treated during 10 min. at 0° with 17.7 g. PhSO2Cl, the mixture kept overnight at 0°, and heated 4 h. with 15.1 g. I gave 6.1 g. 4-hydroxyquinazolinium chloride, m. 293° (decomposition) (EtOCH2CH2OH). The free base m. 232° (Me2CO); picrate m. 274-5° (decomposition) (AcOH); acetyl derivative, prisms, m. 121-2° (C6H6-ligroine). The C5H5N mother liquor from the isolation of the foregoing chloride evaporated, and the residue codistd. with 130 mL. NH4OH gave 3 g. 4-oxoquinazoline, prisms, m. 186-7° (H2O); picrate, prisms, m. 282-4° (decomposition); acetyl derivative, prisms, m. 158-9° (C6H6-ligroine). The following 4-hydroxy-2-substituted-aminoquinazolines were thus obtained (substituent, m.p., % yield, m.p. of picrate, and m.p. of Ac derivative given): Me, 276°, 7, 294°, 196°; Pr, 198.5-200°, 34 (0.5HCl salt m. 292.5-3.5°) 252°, 118-19°; iso-Pr, 212-13°, 45, 264°, 129-30°; Bu, 187-8°, 39 (0.5HCl salt m. 258-9°), 240°; 111-12°; Me(CH2)4, 157.5-9.0°, 40 (0.5HCl salt m. 235°) 215-16°, 60-2°; cyclohexyl, 209-10°, 58 (0.5HCl salt m. 283°) 267°, 204-5°; PhCH2, 213.5-14.5°, 49, 236°, 124-5°; Ph, 261°, 19, 268°, 202-4° p-C6H4Me, 268-9°, 32, semipicrate, 285°; 209°; o-C6H4Me, 287-9°, 41, 255-6°, 154-6°; p-MeOC6H4, 271-2°, 36, -, 204-5°. The following 2-amino-3,4-dihydro-3-substituted-4-oxoquinazolines were thus obtained [3-substituent, m.p., % yield, m.p. of picrate, and m.p. of Ac derivative given]: Me, 242°, 46, 282-3°, 156-7°; Pr, 186-8°, 16.5, 261°, 151-2°; Bu, 192°, 11, 228-9°, acetyl, 140-1°; Me(CH2)4, 177°, 16, 250°, 96°; PhCH2, 202-4°, 9, 270°, 189-90°; Ph, 252°, 23 (HCl salt m. 291-2°), 268-9°; diacetyl, 209°; p-MeOC6H4, 234-6°, 5 (p-toluenesulfonate m. 258-9°), 271-2°; diacetyl, 206-8°. Pentylamine (17.4 g.) in 20 mL. concentrated HCl and 50 mL. H2O treated with 13 g. NaOCN in 100 mL. H2O gave 17.5 g. pentylurea, b17 137-9°; oxime, m. 102°. Methylphenylcyanamide (3 g.) and 7.4 g. o-methoxycarbonylanilinium p-toluenesulfonate in aqueous alkali heated 2 h. at 210° gave 1.3 g. 4-hydroxy-2-N-methylanilinoquinazoline, prisms, m. 197.5-8.5°; p-toluenesulfonate, prisms, m. 173-4° (alc.-Et2O). p-Methoxyphenylcyanamide (9.8 g.) and 11.4 g. 2-diethylaminoethyl chloride HCl salt refluxed 1 h. in 150 mL. alc. containing 3 g. Na gave 11.3 g. (2-diethylaminoethyl)-p-methoxyphenylcyanamide, m. 31-3°, b4 184°, and 1.4 g. tri-p-methoxyphenylisomelamine, m. 212°. 2-Chloro-4-ethoxyquinazoline (II) and PhNHMe refluxed 1 h. in alc. gave 4-ethoxy-2-N-methylanilinoquinazoline, prisms, m. 87-8° (ligroine); picrate m. 189-90° (decomposition). II (2.3 g.) and 1.2 g. p-anisidine refluxed 1 h. in 20 mL. alc. gave 2.9 g. 2-p-anisidino-4-ethoxyquinazoline, prisms, m. 98-9° (ligroine); picrate m. 179-80° (Me2CO). PhSO2Cl (17.7 g.) added at 0° to 19.4 g. o-ureidobenzoate suspended in 30 mL. C5H5N, and kept overnight at 0° gave 4.9 g. Me o-cyanamidobenzoate, m. 105-6° and 3.5 g. 2,4-dihydroxyquinazoline, m. 349-50°. The alkali insoluble fraction yielded 8.1 g. Me o-benzenesulfonylcyanamidobenzoate, prisms, m. 108° (iso-PrOH). 2-Amino-3,4-dihydro-4-oxo-3-phenylquinazoline (1 g.) refluxed 8 h. with 20 mL. 10N NaOH and the Na salt decomposed with AcOH gave 1 g. 2-anilino-4-hydroxyquinazoline (III), m. 261°; acetyl derivative, m. 202-4°. III was formed in 74% yield when 2-amino-4-hydroxyquinazoline (IIIa) was refluxed 24 h. with 10 mol PhNH2. The following quinazolines were similarly produced by analogous rearrangements and identified by comparison of the base and appropriate derivative with known compounds: 4-hydroxy-2-methylamino-, 95%; 2-ethylamino-4-hydroxy-, 75%; 4-hydroxy-2-propylamino-, 50%; 2-benzylamino-4-hydroxy-, 11%; 4-hydroxy-2-p-methoxyanilino-, 100%, also produced by refluxing 4-ethoxy-2-(p-methoxyanilino-) quinazoline 5 h. with 3N HCl. o-Methoxycarbonylanilinium p-toluenesulfonate (32.3 g.) and 19 g. p-MeC6H4SO3H refluxed 3 h. with 8.4 g. dicyandiamide and 200 mL. H2O gave 15.3 g. p-toluenesulfonate, m. 291-2°. This salt gave 2-guanidino-4-hydroxyquinazoline (IV), m. 310-11° (decomposition). IV (2 g.) refluxed 2 h. with 4 g. KOH in 20 mL. (CH2OH)2, diluted with H2O, and neutralized gave 1.3 g. IIIa, m. 315° (decomposition); picrate m. 258-60° (decomposition); acetyl derivative m. 277-80° (EtOCH2CH2OH). Anthranilic acid (137 g.) in 93 mL. concentrated HCl and 1 l. H2O kept 7 wk with cyanamide gave 86 g. IIIa. IIIa (6.4 g.) and 5.4 g. 2-chloroethyl acetate refluxed 45 min. in 100 mL. alc. containing 0.92 g. Na and 0.6 g. NaI, and left overnight gave 0.8 g. 2-amino-3,4-dihydro-3-(= 2-hydroxyethyl)-4-oxoquinazoline, prisms, m. 224° (alc.); picrate m. 220-1°. CH2ClCH2OH did not effect alkylation. Attempted alkylation of 2-acetamido-4-hydroxyquinazoline with 2-chloroethyl acetate gave only 93% IIIa. 4-Hydroxy-2-methylthioquinazoline (3.8 g.) and 4.6 g. 2-diethylaminoethylamine heated 75 min. at 180° gave 4.1 g. 2-(2-diethylaminoethylamino)-4-hydroxyquinazoline, m. 94-6° (aqueous alc.); picrate m. 234-5° (decomposition); MeI derivative, needles, m. 191-2°; methopicrate, needles, m. 194-5° (H2O). IIIa (3.2 g.) and 12.2 g. ethanolamine refluxed together 6 h. gave 1.15 g. 4-hydroxy-2-(2-hydroxyethylamino)quinazoline, m. 249.5-50.0° (H2O); picrate, needles, m. 212-13° (AcOH). A basic byproduct (1.65 g.), possibly 2,4-bis(2-hydroxyethylamino)quinazoline, crystallized from H2O as prisms, m. 162-3°; picrate m. 226-9° (alc.). Butylamine p-toluenesulfonate prepared in iso-PrOH gave needles, m. 122° (EtOAc). 2-Anilino-4-ethoxyquinazoline (IVa) (2.7 g.) refluxed 1 h. in 30 mL. BuOH containing 0.23 g. Na and poured into H2O gave 2.4 g. 2-anilino-5-butoxyquinazoline (V), prisms, m. 82-3° (alc.); picrate m. 182-3°(alc.). Crude 2-anilino-4-chloroquinazoline (1.1 g.) formed from 2-anilino-4-hydroxyquinazoline and POCl3, furnished 0.2 g. V, when refluxed 16 h. with 25 mL. BuOH containing 0.1 g. Na. IVa (5 g.) afforded 2 g. V, when refluxed 16 h. with 5 g. BuBr in 60 mL. alc. and 0.5 g. Na. The following ethers were obtained by transalkylation similar to that described above: 2-anilino-4-pentyloxyquinazoline (70%), needles, m. 118-19° (iso-PrOH), picrate m. 215-16° (decomposition) and 2-anilino-4-benzyloxyquinazoline (78%), needles, m. 11819° (iso-PrOH), picrate m. 215-16° (decomposition). IVa (5.3 g.) refluxed 1 h. with 60 mL. ethanolamine containing 0.5 g. Na and poured into H2O afforded 5 g. 2-anilino-4-(2-hydroxyethylamino)quinazoline (VI), m. 147-9° (PhMe); picrate, prisms, m. 185° (H2O). At 20°, the reaction yield was 5.15 g. VI was stable to alc. alkali and with HNO2 at 10° gave the nitrite, m. 163-5° (decomposition). 2-Chloro-4-(2-hydroxyethylamino)quinazoline (1 g.) and 0.42 g. PhNH2 in 10 mL. H2O refluxed 45 min. with 0.2 mL. HCl, yielded on basification 1.14 g. VI.
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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