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Method for preparing imidazo[2,1-b]thiazole derivative by catalysis of copper salt

A metal copper salt and imidazolo technology, applied in the direction of organic chemistry, etc., to achieve the effects of wide application prospects, high yield, and mild reaction conditions

Inactive Publication Date: 2010-09-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, the disclosed imidazo[2,1-b]thiazole derivatives with practical value have not been used so far to prepare this type of organic compound with pharmaceutical activity by using such a simple and convenient method with mild conditions. compound

Method used

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  • Method for preparing imidazo[2,1-b]thiazole derivative by catalysis of copper salt
  • Method for preparing imidazo[2,1-b]thiazole derivative by catalysis of copper salt
  • Method for preparing imidazo[2,1-b]thiazole derivative by catalysis of copper salt

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] Under nitrogen protection, add 150 mg of 2-mercaptobenzimidazole, TBAF 3H to the reaction tube 2 1.58 g of O, 19 mg of CuI, 21 μL of DMEDA, 313 mg of 1,1-dibromo-2-styrene, 3 mL of DMF, and reacted at 65°C for 24 hours. Cooled to room temperature, added 15 mL of water, extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 3:1) to obtain the product 3-phenylthiazole[3 , 2-a]benzimidazole, 188 mg (75%). Melting point: 138-140℃. 1 H NMR (400MHz, CDCl 3 ): δ7.81(d, J=8.4Hz, 1H), 7.69-7.67(m, 2H), 7.60-7.59(m, 3H), 7.34(t, J=7.6Hz, 1H), 7.24(d, J=8Hz, 1H), 7.08 (t, J=7.8Hz, 1H), 6.61 (s, 1H); 13 C NMR (100MHz, CDCl 3 ): δ157.2, 148.7, 134.2, 130.1, 129.4, 128.9, 128.8, 122.3, 120.4, 119.2, 111.7, 107.1.Anal.Calcd.(%) for C 15 H 10 N 2 S: C, 71.97; H, 4.03; N, 11.19. Found: C, 71.85; H, 4.16; N, 11.05. MS (EI, m / z) 250 (M + ).

Embodiment 2

[0021]

[0022] Under nitrogen protection, add 150 mg of 2-mercaptobenzimidazole, TBAF 3H to the reaction tube 2 1.58 g of O, 19 mg of CuI, 21 μL of DMEDA, 350 mg of 1,1-dibromo-2-p-methoxystyrene, 3 mL of DMF, and reacted at 65°C for 24 hours. Cooled to room temperature, added 15 mL of water, extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and passed through a silica gel column (the volume ratio of petroleum ether and ethyl acetate is 3:1) to obtain the product 3-p-methoxybenzene Thiazo[3,2-a]benzimidazole, 208 mg (74%). Melting point 148-150 ℃. 1 H NMR (400MHz, CDCl 3 ): δ7.80 (d, J=8.4Hz, 1H), 7.58 (d, J=8.4Hz, 2H), 7.33 (t, J=7.8Hz, 1H), 7.25 (d, J=8.4Hz, 1H) ), 7.10-7.05 (m, 3H), 6.53 (s, 1H), 3.94 (s, 3H); 13 CNMR (100MHz, CDCl 3 ): δ160.9, 157.2, 148.7, 134.0, 130.3, 130.1, 123.3, 121.5, 120.3, 119.1, 114.3, 111.6, 106.3, 55.5.Anal.Calcd.(%) for C 16 H 12 N 2 OS: C, 68.55; H, 4.31; N, 9.99. Found: C, 68.49; H, 4.49; N, 9.81....

Embodiment 3

[0024]

[0025] Under nitrogen protection, add 150 mg of 2-mercaptobenzimidazole, TBAF 3H to the reaction tube 2 1.58 g of O, 19 mg of CuI, 21 μL of DMEDA, 366 mg of 1,1-dibromo-2-p-nitrostyrene, 3 mL of DMF, and reacted at 65°C for 24 hours. Cooled to room temperature, added 15 mL of water, extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and passed through a silica gel column (the volume ratio of petroleum ether and ethyl acetate is 1:1) to obtain the product 3-p-nitrophenyl Thiazo[3,2-a]benzimidazole, 268 mg (90%). Melting point: 258-260°C. 1H NMR (400 MHz, d6-DMSO): δ 7.46 (d, J=8.0 Hz, 2H), 8.06 (d, J=8.8 Hz, 2H), 7.73 (d, J=8.4 Hz, 1H), 7.47 ( s, 1H), 7.34 (t, J=7.6Hz, 1H), 7.25 (d, J=8Hz, 1H), 7.14 (t, J=7.6Hz, 1H); 13 C NMR (100MHz, d6-DMSO): δ 148.5, 135.5, 131.9, 130.4, 124.6, 123.7, 121.0, 119.3, 112.2, 112.0. HRMS (ESI, m / z) Calcd for C 15 H 10 N 3 O 2 S: 296.0494 (M+H) + .Found: 296.0492.

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Abstract

The invention discloses a method for preparing an imidazo[2,1-b]thiazole derivative by catalysis of a copper salt. In an environment of an organic solvent, the copper salt is taken as a catalyst, 1,1-dibromo-1-olefin or alkynyl bromide and a 2-mercaptoimidazole compound are taken as substrates to synthesize the imidazo[1,5-b]thiazole derivative under the action of alkali by one step, wherein the molar ratio of the 2-mercaptoimidazole compound to the 1,1-dibromo-1-olefin or alkynyl bromide is 1:1-1:5; the molar ratio of the 2-mercaptoimidazole compound to the alkali is 1:3-1:8; based on the 2-mercaptoimidazole compound, the using amount of the copper salt is 0.1 percent to 3.0 mol percent; the molar ratio of a ligand to the copper salt is 1:2-2:1; and the reaction temperature is 20 to 110 DEG C. The preparation method is simple and mild in reaction conditions, and has wide application prospect in fine chemical industry and pharmacy industry.

Description

technical field [0001] The invention relates to a preparation method of imidazo[2,1-b]thiazole derivatives catalyzed by metal copper salts. Background technique [0002] As an important class of organic fused heterocyclic compounds, imidazo[2,1-b]thiazole derivatives have important biological and pharmaceutical activities, such as anticancer, antitumor, treatment of diabetes, etc. (Milne, J.C.; Lambert, P.D. ; Schenk, S.; Carney, D.P.; Smith, J.J.; Gagne, D.J.; Jin, L.; Boss, O.; Perni, R.B.; Vu, C.B.; Bemis, J.E.; Xie, R.; Disch, J.S.; Ng , P.Y.; Nunes, J.J.; Lynch, A.V.; Yang, H.; Galonek, H.; Israelian, K.; Choy, W.; Iffland, A.; Lavu, S.; Medvedik, O.; Sinclair, D.A.; Olefsky, J.M.; Jirousek, M.R.; Elliott, P.J.; Westphal, C.H. Nature, 2007, 450, 712-716), so it has broad application prospects in the pharmaceutical industry. In the past preparation methods, multi-step synthesis was often used with low yields (Singh, S.; Singh, H.; Singh, M.; Narang, K.S.Ind.J.Chem., 19...

Claims

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Application Information

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IPC IPC(8): C07D513/04
Inventor 陈万芝徐辉
Owner ZHEJIANG UNIV
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