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Method for preparing 2-amino-4(3H)-quinazolinones
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A technology for aminoquinazoline and ketone compounds, which is applied in the field of catalytic preparation of 2-aminoquinazoline-4-one compounds, can solve the problem of high reaction cost, process complexity, complicated and rare starting materials, harsh reaction conditions, etc. problems, to achieve the effect of simple and controllable preparation process, simple post-processing, and short reaction time
Inactive Publication Date: 2015-04-22
SUZHOU UNIV
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[0007] In addition to these types of methods, there are still some synthetic routes, some of which require complex and rare starting materials, some require high pressure conditions, and the reaction cost and complexity of the process are relatively high.
[0008] Although the synthetic methods currently reported can prepare 2-aminoquinazolin-4-one compounds, they generally have various defects, such as expensive precursors or complicated preparations, too many reaction steps, harsh reaction conditions, etc.; therefore, the development of A green and environmentally friendly approach to the efficient catalytic synthesis of 2-aminoquinazolin-4-one compounds under mild and convenient conditions is necessary
[0009] Another bimetallic cationic complex [Ln(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN is a kind of homogeneous catalyst, which can catalyze the polymerization and isomerization of olefins and cycloolefins, and its synthesis method has been reported (see: Hu Jingyu; Shen Qi; Jin Zhongsheng. A new type of rare earthacetonitrile cation complex [Ln( CH 3 EN) 9 (AlCl 4 ) 3 ] CH 3 Synthesis of CN. Scientific Bulletin 1989, 34, 1554), but the application of such complexes in the synthesis of 2-aminoquinazolin-4-one compounds has not been reported
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[0038] In the reaction bottle that has been dehydrated and deoxygenated, under the protection of argon, weigh 0.61 g (2.5 mmol) of LaCl at a molar ratio of 1:3. 3 and 1.00 g (7.5 mmol) of anhydrous AlCl 3 , add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and put it in a refrigerator at 0°C, the obtained crystal is [La(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN, the yield is 40%.
[0039] The product is white, elemental analysis: La, (13.16±0.5)%, Cl, (40.29±0.5)%.
[0041] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, weigh 0.63 g (2.5 mmol) of NdCl at a molar ratio of 1:3 3 and 1.00 g (7.5 mmol) of anhydrous AlCl 3 , add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and put it in a refrigerator at 0°C, the obtained crystal is [Nd (CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN, yield 45%.
[0044] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, weigh 0.64 g (2.5 mmol) of SmCl at a molar ratio of 1:3 3 and 1.00 g (7.5 mmol) of anhydrous AlCl 3 , add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and put it in a refrigerator at 0°C, the obtained crystal is [Sm (CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– ·CH 3 CN, the yield is 53%.
[0045] The product is light yellow, elemental analysis: Sm, (14.10±0.5)%, Cl, (39.90±0.5)%.
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Abstract
The invention discloses a method for preparing 2-amino-4(3H)-quinazolinones. Specifically, a bimetallic cationic complex [Ln(CH3CHN)9]<3+>[(AlCl4)3]<3->.CH3CN is taken as a catalyst, a methyl 2-aminobenzoate compound and a carbodiimide compound are catalyzed for preparation of 2-amino-4(3H)-quinazolinones, wherein Ln represents a positive trivalent rare earthmetalion and is one selected from lanthanum, neodymium, samarium, gadolinium, erbium and ytterbium, CH3CN represents acetonitrile, and the chemical structural general formula of methyl 2-aminobenzoates and the general formula of carbodiimides are both shown in the description. The bimetallic cationic catalyst disclosed by the invention has high activity and has universality for multiple methyl 2-aminobenzoates and carbodiimides; the preparation method is short in reaction time, mild in reaction conditions, high in target product yield, and simple and controllable in preparation process, and has industrialization application potential.
Description
technical field [0001] The invention belongs to the technical field of preparation of organic nitrogen heterocyclic compounds, and in particular relates to a catalytic preparation method of 2-aminoquinazolin-4-one compounds. Background technique [0002] Quinazoline structural units widely exist in biologically active natural products and drug molecules, and compounds containing 2-aminoquinazolin-4-one skeletons have been confirmed to have a variety of important biological activities. focus on. [0003] In the prior art, the commonly used method of synthesizing 2-aminoquinazolin-4-one compound mainly contains following three kinds: [0004] 1. A 2-aminoquinazolin-4-one compound is obtained through a nucleophilic substitution reaction at the 2-position of the quinazoline mother ring and an amine. For example, J. DeRuiter prepared 2-aminoquinazolin-4-one compound by reacting 2-chloroquinazolin-4-one with aniline or benzylamine in DMF solvent at 80-100°C for 1-5 hours. 56~89...
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