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Synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof

A technology of benzothiazole and benzoxazole, applied in the field of benzoxazole and 2-substituted benzothiazole and derivatives thereof, can solve problems such as inconsistency with atom economy, and achieve excellent yield and purity, The effect of short reaction time and high process economy

Active Publication Date: 2019-01-25
CHONGQING MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method using 4-8 equivalents of oxalic acid / malonic acid is not atom-economical (P.Das.Org.Biomol.Chem.2018:16:1337)

Method used

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  • Synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof
  • Synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof
  • Synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof

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Embodiment 1

[0052] Example 1 General method for the synthesis of 2-substituted benzoxazole and 2-substituted benzothiazole derivatives (2a, 2c, 2f, 2g, 4a-d)

[0053] To a 10 mL three-necked round flask was added 1a (0.6 g, 5.5 mmol, 1 equivalent), imidazole hydrochloric acid (0.28 g, 2.75 mmol, 0.5 equivalent) and 5 mL of N,N-dimethylacetamide. The resulting solution was warmed to 160° C. and the reaction was stirred at this temperature. TLC spot detection was performed. When the reaction was complete, 25 mL of water was added, and the resulting mixture was extracted twice with 25 mL of ethyl acetate. The combined organic layer was washed sequentially with H 2 O (50 mL), then brine (50 mL), then dried over anhydrous Na 2 SO 4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallized with petroleum ether and ethyl acetate or petroleum ether / ethyl acetate to obtain the target product.

[0054] General method for the synth...

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Abstract

The invention provides a synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof. In the method, through ortho-aminophenol / 2-aminothiophenol cyclization catalyzed by imidazole hydrochloride, synthesis of functionalized 2-substituted benzoxazole and 2-substituted benzothiazole is realized; the method is simple, economical and high in practicality. No othercatalysts or additives are used, the synthesis method ensures good functional group tolerance and excellent yield and purity, the reaction time is short, no harsh reaction conditions are needed, andthe method is suitable for industrial production.

Description

Technical field [0001] The present invention relates to 2-substituted benzoxazole and 2-substituted benzothiazole and their derivatives, in particular to the synthesis of a 2-substituted benzoxazole and 2-substituted benzothiazole and their derivatives method. Background technique [0002] 2-substituted benzoxazole compounds are a class of benzoheterocyclic compounds containing one nitrogen atom and one oxygen atom, 2-substituted benzothiazole compounds are a class of benzene containing one nitrogen atom and one sulfur atom Heterocyclic compounds, these compounds are the structural unit of many drugs (Kaplancikli ZA, Gülhan Turan Zitouni, Revial ​​G, Guven K, Archives of Pharmacal Research. 2004:27:1081; Viirre RD, Evindar G, Batey RA. Journal of Organic Chemistry. 2008:39:3452.). The traditional synthesis method of benzoxazoles and benzothiazoles is mainly through the condensation of o-aminophenol / thiophenol with aldehydes, acids, amides, acid chlorides, nitriles, esters or th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/56C07D263/57C07D277/64C07D277/66C07D417/04
CPCC07D263/56C07D263/57C07D277/64C07D277/66C07D417/04
Inventor 袁建勇代泽树田青强罗雯李丹
Owner CHONGQING MEDICAL UNIVERSITY
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