CN113788812B - 一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 - Google Patents
一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 Download PDFInfo
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Abstract
本发明公开了一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法,属于有机化学及光催化领域。该方法以ZnIn2S4作为光催化剂,在可见光的条件下,在N2气氛中通过苯乙炔与烯丙基硫醇的发生环化反应生成二氢噻吩,产率良好,同时制备该催化剂的方法简便易行,后处理过程中产物与催化剂易分离。
Description
技术领域
本发明属于有机化学及光催化领域,具体涉及到一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法。
背景技术
噻吩是五元含硫杂环化合物,最初是从煤焦油中发现的。噻吩及其衍生物具有广泛的生物或药理活性。杂环化合物二氢噻吩广泛分布于许多天然产物中,是一类具有生物活性的化合物,具有重要的药用价值和生物活性。另一方面,二氢噻吩也是许多化合物(包括噻吩,硫代核苷衍生物和青霉素)的重要合成前驱体。目前,含有噻吩母核结构的药物已超过两百多种。而且在研究中发现,噻吩结构对有些药物活性的影响远远高于苯环结构。一些新的临床药物,如治疗老年男性骨质疏松症的药物雷诺昔吩,用于治疗抑郁症和综合焦虑失调症的度洛西汀,俗称欣百达药物,长效吸入型支气管扩张药噻托溴铵,以及治疗青光眼的药物可速普特都是含有噻吩结构单元的药物。此外,噻吩还可用来合成功能性材料和食用香料等物质。因此,探究一种绿色、高效的二氢噻吩合成方法显得尤为重要且颇有意义。
发明内容
本发明的目的在于提供一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法,。该方法以ZnIn2S4作为光催化剂,在可见光的条件下,在N2气氛中通过苯乙炔与烯丙基硫醇的环化反应生成二氢噻吩,产率良好,同时制备该催化剂的方法简便易行,后处理过程中产物与催化剂易分离。
为实现上述目的,本发明采用如下技术方案:
以ZnIn2S4作为光催化剂,在可见光的条件下,在N2气氛中通过苯乙炔与烯丙基硫醇的环化反应生成二氢噻吩。具体步骤为:将10 mg催化剂ZnIn2S4、0.1 mmol苯乙炔和0.1mmol烯丙基硫醇加入装有溶剂甲醇(CH3OH, 2 ml)的Schlenk反应管,经过三次脱气、鼓气操作,使反应气氛为N2。在室温条件下,从反应管底部利用65 mW/cm2的LED灯照射15 h,反应过程中保持持续搅拌的操作。反应结束后,取出反应液并通过多孔膜(直径为20 μm)过滤,得到的滤液通过配备HP-5毛细管柱的GC-MS(Agilent 7890B-5977A)和GC-FID(Shimadzu2014)进行分析,并用LC-MS(Agilent X Series 2)辅助分析产物的组成。
上述所用光催化剂ZnIn2S4的制备方法,包括以下步骤:
通过双溶剂法制备催化剂ZnIn2S4,将前驱物ZnCl2(1 mmol)、InCl3·4H2O(2 mmol)和硫代乙酰胺(TAA, 4 mmol)按照顺序分别加入30 ml乙二醇(EG)和30 ml N,N-二甲基甲酰胺(DMF)的混合溶液中,并超声直至固体在溶液中分散均匀,持续搅拌1小时左右,再将混合液全部转移至100 ml 聚四氟乙烯反应釜中。密封后将反应釜放入烘箱中,反应温度为180 ℃,反应24 h,自然冷却至室温后将产物取出,分别经无水乙醇和去离子水离心洗涤3次,烘干,得到亮黄色产物ZnIn2S4。
本发明的显著优点在于:
(1)本发明在温和条件下实现了光催化环化反应合成二氢噻吩,烯丙基硫醇在ZnIn2S4光催化下生成相应的巯基自由基,在温和条件下与苯乙炔进行成环反应,生成相应的二氢噻吩产物,具有实际应用价值。
(2)本发明光催化剂的制备方法简单易行,价格低廉且没有金属残留,具有后处理产物与催化剂易分离的特点,催化剂可以重复利用。
具体实施方式
下面结合实施例对本发明进一步详细说明,需要指出的是,以下所述实施例旨在便于对本发明的理解,而对其不起任何限定作用。
光催化剂ZnIn2S4催化苯乙炔与烯丙基硫醇环化反应的活性测试在N2气氛下进行,反应温度为室温。具体步骤为:将10 mg催化剂ZnIn2S4、0.1 mmol苯乙炔和0.1 mmol烯丙基硫醇加入装有溶剂甲醇(CH3OH, 2 ml)的Schlenk反应管,经过三次脱气、鼓气操作,使反应气氛为N2。在室温条件下,从反应管底部利用65 mW/cm2的LED灯照射15 h,反应过程中保持持续搅拌的操作。反应结束后,取出反应液并通过多孔膜(直径为20 μm)过滤,得到的滤液通过配备HP-5毛细管柱的GC-MS(Agilent 7890B-5977A)和GC-FID(Shimadzu 2014)进行分析,并用LC-MS(Agilent X Series 2)辅助分析产物的组成。
光催化剂的具体制备步骤如下:
将前驱物ZnCl2(1 mmol)、InCl3·4H2O(2 mmol)和硫代乙酰胺(TAA, 4 mmol)按照顺序分别加入30 ml乙二醇(EG)和30 ml N,N-二甲基甲酰胺(DMF)的混合溶液中,并超声直至固体在溶液中分散均匀,持续搅拌1小时左右,再将混合液全部转移至100 ml 聚四氟乙烯反应釜中。密封后将反应釜放入烘箱中,反应温度为180 ℃,反应24 h,自然冷却至室温后将产物取出,分别经无水乙醇和去离子水离心洗涤3次,烘干,得到亮黄色产物ZnIn2S4。
实施例1
以10 mg ZnIn2S4作催化剂,苯乙炔和烯丙硫醇作为底物,甲醇作溶剂,在N2气氛保护下,使用65 mW/cm2LED灯光照15 h,底物苯乙炔的转化率为76.6%,二氢噻吩的产率为50.1%。在没有光照射和不加光催化剂的情况下,底物并没有发生转化,可以得出光照和光催化剂是本反应的必要条件。
表1 光催化苯乙炔和烯丙基硫醇成环反应条件探索
实施例2
在甲醇为溶剂、ZnIn2S4作催化剂、N2气氛下,利用LED灯光照15 h,选用不同取代基的炔烃进行底物拓展反应,当炔烃为苯环上连有不同取代基的苯乙炔时,该成环反应可以顺利进行(序号1-4),73.3%的对甲基苯乙炔被转化,生成49.1%的3-对甲基苯基-4-甲基-4,5-二氢噻吩(序号1),对乙基苯乙炔以48.4%的产率生成3-对乙基苯基-4-甲基-4,5-二氢噻吩(序号2),对氨基苯乙炔以42.3%的产率生成3-对氨基苯基-4-甲基-4,5-二氢噻吩(序号3),对硝基苯乙炔则以40.6%的产率生成3-对硝基苯基-4-甲基-4,5-二氢噻吩(序号4),从上述结果可以发现电子效应对反应的影响并不明显,说明本反应底物适应性良好。
表2 光催化苯乙炔和烯丙基硫醇成环反应的底物适用性探究
以上所述仅为本发明的较佳实施例,凡依本发明申请专利范围所做的均等变化与修饰,皆应属本发明的涵盖范围。
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