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Synthesis method of 5,6-2H-pyrrolo[1,5-c] quinazoline compounds

A quinazoline and dihydropyrazole technology, which is applied in the field of synthesis of 5,6-dihydropyrazolo[1,5-c]quinazoline compounds, can solve the problem of difficult mass preparation and limited application Scope, limitations, etc.

Inactive Publication Date: 2013-06-05
HENAN NORMAL UNIV
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Problems solved by technology

These traditional synthetic methods often need to be carried out smoothly under the promotion of strong acid or strong base, which limits the scope of application of this type of synthetic method to a large extent, and more importantly, the raw material 5-(2-amine used in the reaction Phenylphenyl)-pyrazoles are difficult to prepare in large quantities, therefore, they are greatly restricted in actual production

Method used

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  • Synthesis method of 5,6-2H-pyrrolo[1,5-c] quinazoline compounds
  • Synthesis method of 5,6-2H-pyrrolo[1,5-c] quinazoline compounds
  • Synthesis method of 5,6-2H-pyrrolo[1,5-c] quinazoline compounds

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Embodiment 1

[0016]

[0017] Add to a 25 mL reaction tube 1a (0.4 mmol, 95 mg), 2a (1.6 mmol, 93 mg), cuprous iodide (0.04 mmol, 7.6 mg) and N,N-dimethylformamide (2 mL), then add concentrated ammonia (NH 3 ·H 2 O: 2.8 mmol, 0.4 mL). Heat to 100 under air o C. After stirring for 4 hours, the reaction was quenched by adding 5 mL of saturated ammonium chloride solution, extracted with ethyl acetate (10 mL × 2), and then the organic phase was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate = 5 / 1) to obtain the white solid product 2,5,5-trimethyl-5,6-dihydropyrazolo[1,5- c ] quinazoline 3a (46 mg, 54%). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 , 400 MHz) δ 1.72 (s, 6H), 2.34 (s, 3H), 4.20 (brs, 1H), 6.28 (s, 1H), 6.71 (d, J = 8.0 Hz, 1H), 6.85 (t, J = 7.6 Hz, 1H), 7.11-7.15 (m, 1H), 7.39-7.41 (m, 1H); 13 C NMR (...

Embodiment 2

[0019]

[0020] According to the method described in Example 1, add 1a (0.4 mmol, 95 mg), 2b (0.8 mmol, 78 mg), cuprous chloride (0.04 mmol, 4.0 mg) and N,N-dimethylformamide (2 mL), then add concentrated ammonia (NH 3 ·H 2 O: 2.8 mmol, 0.4 mL). Heat to 100 under air o C, after stirring for 4 hours, the white solid product 2'-methyl-6' was obtained H -Spiro[cyclohexane-1,5'-pyrazolo[1,5- c ]quinazoline] 3b (70 mg, 69%) (petroleum ether / ethyl acetate = 8 / 1). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 , 400 MHz) δ 1.27-1.37 (m, 2H), 1.43-1.53 ​​(m, 2H), 1.70-1.81 (m, 2H), 2.00-2.03 (m, 2H), 2.19 (dt, J = 4.0, 13,2 Hz, 2H), 2.34 (s, 3H), 4.60 (brs, 1H), 6.28 (s, 1H), 6.76 (d, J = 8.0 Hz, 1H), 6.85 (t, J = 7.2 Hz, 1H), 7.10-7.14 (m, 1H), 7.39 (d, J = 7.6 Hz, 1H); 13 C NMR (CDCl 3 , 100 MHz) δ 13.9, 22.3, 24.6, 34.6, 72.9, 99.5, 115.4, 115.8, 119.7, 123.8, 129.0, 137.4, 138.7, 148.4. HRMS (ESI) calcd for C 16 h 20 N 3 [M+H]...

Embodiment 3

[0022]

[0023] According to the method described in Example 1, add 1b (0.4 mmol, 120 mg), 2a (1.6 mmol, 93 mg), cuprous iodide (0.04 mmol, 7.6 mg) and dimethyl sulfoxide (2 mL), then add concentrated ammonia (NH 3 ·H 2 O: 2.8 mmol, 0.4 mL). Heat to 80 under air o C, after stirring for 12 hours, the white solid product 2-phenyl-5,5-dimethyl-5,6-dihydropyrazolo[1,5- c ] quinazoline 3c (61 mg, 55%) (petroleum ether / ethyl acetate = 8 / 1). The characterization data of this compound are as follows: 1 H NMR (CDCl 3 , 400 MHz) δ 1.80 (s, 6H), 4.13 (brs, 1H), 6.75 (d, J = 8.0 Hz, 1H), 6.80 (s, 1H), 6.91 (t, J = 8.0 Hz, 1H), 7.17 (t, J = 8.0 Hz, 1H), 7.31 (t, J = 7.2 Hz, 1H), 7.42 (t, J = 7.6 Hz, 2H), 7.51 (d, J = 7.2 Hz, 1H), 7.88 (d, J = 7.2 Hz, 2H); 13 C NMR (CDCl 3, 100 MHz) δ 28.0, 72.3, 96.9, 114.8, 115.5, 119.9, 124.0, 125.8, 127.6, 128.6, 129.2, 133.7, 137.6, 139.2, 151.3. HRMS (ESI) calcd for C 18 h 18 N 3 [M+H] + : 276.1495, found: 276.1506.

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Abstract

The invention discloses a synthesis method of 5,6-2H-pyrrolo[1,5-c] quinazoline compounds. The technical scheme has the key points as follows: the synthesis method of the 5,6-2H-pyrrolo[1,5-c] quinazoline compounds is used for synthesizing various types of 5,6-2H-pyrrolo[1,5-c] quinazoline compounds at one step on the basis of simply and easily prepared 5-(2-bromoaryl)-1H-pyrazol through cascade reaction among 5-(2-bromoaryl)-1H-pyrazol, ammonia water and multiple components of a ketone compound. The synthesis method disclosed by the invention has the advantages of simply and easily prepared initial raw materials, wide substrate application range, easily separated and purified products and the like.

Description

[0001] technical field [0002] The invention belongs to the technical field of organic synthesis, in particular to a 5,6-dihydropyrazolo[1,5- c ] The synthetic method of quinazoline compounds. Background technique [0003] Nitrogen-fused heterocyclic skeletons widely exist in alkaloids and have attracted extensive attention from chemists and pharmacologists in recent years. Among them, 5,6-dihydropyrazolo[1,5- c ]Quinazoline compounds have broad-spectrum physiological and biological activities, and have important development and application values ​​in the fields of biology and medicine. The 5,6-dihydropyrazolo[1,5- c ] The synthetic method of quinazolines is mainly prepared by the condensation reaction of 5-(2-aminophenyl)-pyrazole with aldehydes or ketones. These traditional synthetic methods often need to be carried out smoothly under the promotion of strong acid or strong base, which limits the scope of application of this type of synthetic method to a large extent....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 范学森郭胜海王继亮张新迎王强郭东强
Owner HENAN NORMAL UNIV
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