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Method for preparing 5-aminotetrazole compound

A technology for aminotetrazoles and compounds, which is applied in the field of preparation of 5-aminotetrazoles, can solve the problems of using heavy metal reagents, harsh reaction conditions, and long reaction time, so as to avoid the use of heavy metals and mild reaction conditions , The effect of high product yield

Active Publication Date: 2016-04-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] A lot of documents have reported the synthetic method of aminotetrazole derivatives, such as people such as Finnegan in 1953, prepared aminotetrazolium compounds through diazotization and cyclization reaction with aminoguanidine as raw material, the process steps are loaded down with trivial details, reaction conditions Strict requirements; in 1980, Tsuge et al. used TMSA as a cyclization reagent, put carbodiimide in a mixed solvent of benzene and methanol to reflux, and could synthesize aminotetrazole with a higher yield, but the solvent benzene is more toxic
There are many other methods, but the reaction conditions of most methods are relatively harsh, using heavy metal reagents or toxic reagents, and the reaction time is long

Method used

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  • Method for preparing 5-aminotetrazole compound
  • Method for preparing 5-aminotetrazole compound
  • Method for preparing 5-aminotetrazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Add 1,3-diphenylselenourea (275mg, 1mmol), ionic liquid-loaded iodobenzene diacetate (674mg, 1.2mmol) and sodium azide (195mg, 3mmol) into a 50mL single-necked bottle, add DMF (10mL ) and H 2 O (1 mL), NaOH (80 mg, 2 mmol) was added, and stirred at 25° C. for 0.2 h. After the TLC monitoring reaction finishes, filter, pour the filtrate into saturated NaHCO 3 In the aqueous solution, the layers were allowed to stand, and the obtained aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with anhydrous Na 2 SO 4 After drying and concentration, it was separated by column chromatography (eluent petroleum ether: ethyl acetate volume ratio = 4:1). The eluate containing the product was collected, and the solvent was evaporated to obtain the white target product Ia with a yield of 0.225 g and a yield of 95% (document 76%: New Journal of Chemistry, 2013, 37(2), 488-493).

[0042] Melting point: 158-160°C (literature 158-159°C)...

Embodiment 2

[0044]

[0045] Add 1,3-di-o-ethylphenylselenourea (331mg, 1mmol), ionic liquid-loaded iodobenzene diacetate (450mg, 0.8mmol) and sodium azide (260mg, 4mmol) into a 50mL single-necked bottle, add Dimethylsulfoxide (15mL) and H 2 O (2mL), then add Cs 2 CO 3 (326mg, 1mmol), stirred at 50°C for 1h. After the TLC monitoring reaction finishes, filter, pour the filtrate into saturated NaHCO 3 In the aqueous solution, the layers were allowed to stand, and the obtained aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with anhydrous Na 2 SO 4 After drying and concentration, it was separated by column chromatography (eluent petroleum ether: ethyl acetate volume ratio = 4:1). The eluate containing the product was collected, and the solvent was distilled off to obtain the white target product Ib with a yield of 0.152 g and a yield of 52%.

[0046] Melting point: 109-111°C; 1 HNMR (400MHz, CDCl 3 )δ8.10(d,J=8.0Hz,1H),7.58(td,J 1 =7.6...

Embodiment 3

[0048]

[0049] Add 1,3-di-p-chlorophenylselenourea (344mg, 1mmol), ionic liquid-loaded iodobenzene diacetate (843mg, 1.5mmol) and sodium azide (130mg, 2mmol) into a 50mL single-necked bottle, add toluene (30mL) and H 2 O (0.1 mL), then added KOH (140 mg, 2.5 mmol), stirred at 80° C. for 0.1 h. After the TLC monitoring reaction finishes, filter, pour the filtrate into saturated NaHCO 3 In the aqueous solution, the layers were allowed to stand, and the obtained aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with anhydrous Na 2 SO 4 After drying and concentration, it was separated by column chromatography (eluent petroleum ether: ethyl acetate volume ratio = 4:1). The eluate containing the product was collected, and the solvent was distilled off to obtain the white target product Ic, with a yield of 0.217 g and a yield of 71%.

[0050] Melting point: 194-195°C; IR(KBr)ν max 3271, 2920, 1610, 1570, 1491, 1410, 1090, 820; 1 HNM...

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Abstract

The invention discloses a method for preparing a 5-aminotetrazole compound. The method comprises the following steps: adding bis-substituted selenourea shown in the formula II in the description, ionic liquid loaded iodobenzene diacetate shown in the formula III in the description, sodium azide and alkali A into a solvent B, stirring at -10 to -80 DEG C and conducting cyclization reaction, and after the reaction is finished, conducting aftertreatment on the reaction liquid to prepare the 5-aminotetrazole compound shown in the formula I in the description. Compared with the conventional method, a green reagent, namely, ionic liquid loaded iodobenzene diacetate, is adopted, so that the use of heavy metal is avoided, the operation is simple and convenient, and the reaction yield is high.

Description

1. Technical field [0001] The invention relates to a preparation method of 5-aminotetrazole compounds, belonging to the field of organic synthesis. 2. Background technology [0002] Tetrazolium compounds are five-membered heterocyclic compounds containing four nitrogen atoms, with high nitrogen content and good stability. The tetrazole ring can be used as the bioisostere of the carboxyl group, which plays an important role in improving the biological activity and pharmacokinetics of the compound. As an important class of intermediates, aminotetrazolium compounds are widely used in the synthesis of drugs, so the synthesis of 5-aminotetrazole skeleton is a very active research direction. [0003] Many aminotetrazolium derivatives have biological activities such as anti-allergic, anti-viral, anti-inflammatory, anti-tumor, etc. A typical example is the anti-HIV drug 3'-(5-amino-1,2,3,4-tetrazol-1-yl)-3'-deoxythymidine and its derivatives (Habich , D. Synthesis, 1992, 4, 358-3...

Claims

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Application Information

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IPC IPC(8): C07D257/06B01J31/02
CPCB01J31/0285C07D257/06
Inventor 谢媛媛蒋筱莹郭冬艳王文慧米治胜金婷婷
Owner ZHEJIANG UNIV OF TECH
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