Heterocycle substituted triazole compound and synthetic method thereof

A compound, triazole technology, applied in the field of pharmaceutical intermediate compounds and their synthesis, can solve the problems of long reaction time, large environmental pollution and the like

Inactive Publication Date: 2009-05-06
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Recently, someone used monovalent copper salts (such as CuI, CuCl, etc.) to catalyze the 1,3-dipolar cycloaddition reaction of azido-based organic compounds and substituted alkynes to success

Method used

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  • Heterocycle substituted triazole compound and synthetic method thereof
  • Heterocycle substituted triazole compound and synthetic method thereof
  • Heterocycle substituted triazole compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1. The preparation of 1-(2-chloroethyl)indole, according to the literature Dariusz Bogdal and Knysztof Jaskot, SYNTHETIC COMMUNICATIONS, 2000, 30(18), 3341-3352.

[0031] 2. Suspend 1-(2-chloroethyl)indole (0.2mol) in 20ml of water, add sodium azide (0.24mol), phenylacetylene (0.22mol) and cuprous iodide (0.006mol), and finally Add PEG-600 (0.04mol), stir at 20-30°C for 8 hours, filter, wash with dilute ammonia (2 x 15ml), wash with water (2 x 10ml), wash with hexane (3 x 10ml) and dry. Yield 79%. 1 H NMR (500MHz, CDCl 3 )δ 7.63-7.65(d, 2H, J=7.8Hz), 7.59-7.61(m, 3H), 7.11-7.37(m, 4H), 6.93(s, 1H), 6.75(d, 1H, J=2.65 Hz), 6.45(d, 1H, J=2.35Hz), 4.74(t, 2H, J=10.85Hz), 4.65(t, 2H, J=10.95Hz); 13 C NMR (500MHz, CDCl 3 )δ 46.91, 50.29, 102.91, 109.10, 120.49, 121.22, 121.82, 122.63, 126.15, 128.60, 129.17, 130.70, 135.88, 148.30;

Embodiment 2

[0033] 1. Preparation of 2-bromomethylbenzimidazole. In the there-necked flask of 100 milliliters that is added with 60 milliliters of carbon tetrachlorides, add 2-methylbenzimidazole (0.42mol), NBS (0.45mol) and benzoyl peroxide (1mol%), under magnetic stirring (Nitrogen was introduced as a protective gas), heated to reflux for 5 hours until the reaction was complete (TLC detection), and the product was obtained with a yield of 97%.

[0034] 2. Suspend 2-bromomethylbenzimidazole (0.2mol) in 20ml of water, add sodium azide (0.24mol), phenylacetylene (0.22mol) and cuprous iodide (0.005mol), and finally add TBAB ( 0.05mol), stirred at 20-30°C for 3 hours, filtered, washed with dilute ammonia (2 x 15ml), washed with water (2 x 10ml), washed with hexane (3 x 10ml) and dried. Yield 93%. m.p.210~211℃. MS m / z=275; 1 H NMR (500MHz, DMSO) δ12.70(s, 1H), 8.71(s, 1H), 7.90(d, 2H, J=7.55Hz), 7.62(d, 2H), 7.44-7.52(m, 2H) , 7.21-7.36(m, 3H), 5.94(s, 2H); 13 CNMR (500MHz, DMSO) δ 47.96...

Embodiment 3

[0036] 1. Preparation of 9-(2-chloroethyl)carbazole. According to Dariusz Bogdal and Knysztof Jaskot, SYNTHETIC COMMUNICATIONS, 2000, 30(18), 3341-3352.

[0037] 2. Suspend 9-(2-chloroethyl)carbazole (0.2mol) in 20ml of water, add sodium azide (0.24mol), phenylacetylene (0.22mol) and cuprous iodide (0.005mol), and finally Add TBAB (0.05mol), stir and react at 20-30°C for 10 hours, filter, wash with dilute ammonia (2 x 15ml), water (2 x 10ml), hexane (3 x 10ml) and dry. Yield 82%. MS m / z = 338. 1 H NMR (500MHz, CDCl 3 )δ 7.99(d, 2H, J=7.7Hz), 7.92(d, 2H, J=7.75Hz), 7.40-7.58(m, 5H), 7.00-7.38(m, 4H), 6.91(d, 2H) , 4.92(t, 2H, J=11.7Hz), 4.87(t, 2H, J=11.45Hz);

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Abstract

The invention relates to a heterocycle 1, 4-disubstituted-1, 2, 3-triazole compound and a synthesizing method thereof. A halomethylated heterocycle compound and sodium azide and terminal alkyne compounds generate 1, 3-dipolar cycloaddition reaction through simple process and mild condition under the action of a phase transfer catalyst to synthesize the heterocycle 1, 4-disubstituted-1, 2, 3-triazole derivative with high selectivity and high yield. The compound is an important medicinal intermediate, and simultaneously has potential in pesticide, fine chemistry industry and other fields. In the formula of the compound, heterocycle-1, 4 is a nitrogen heterocyclic ring: imidazole and derivatives thereof, benzoglioxaline and derivatives thereof, benzotriazol, indole and derivatives thereof, carbazole and derivatives thereof; Y is H or F, n is equal to between 1 and 8; and r presents Ar, Alk and Bn.

Description

Technical field [0001] The invention relates to a pharmaceutical intermediate compound and a synthesis method thereof, in particular to a heterocyclic substituted triazole compound and a synthesis method thereof. Background technique [0002] Since the bactericidal activity of azole compounds was discovered in the late 1960s, they have reached a new level in the control of pathogenic bacteria that harm plants and humans. The traditional imidazole drug ketoconazole is no longer used for deep fungal infections due to severe toxic and side effects. The beginning of the drug-like era. The toxicity of azoles is related to its selectivity to fungal and mammalian enzymes, because the selectivity of triazoles to fungal enzymes is higher than that of imidazoles, while the selectivity to mammalian enzymes Lower than imidazoles, so triazoles are less toxic than imidazoles. [0003] In the 1970s, the high-efficiency bactericidal activity of triazole compounds attracted great attentio...

Claims

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Application Information

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IPC IPC(8): C07D403/06
Inventor 王锐朱称水高杨马林转段利平张灿王超金诚
Owner YUNNAN MINZU UNIV
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