新型咔唑衍生物的合成研究
摘要
咔唑衍生物主要用于合成染(颜)料、农药、医药和合成树脂等领域,而且是很好的非线性光学材料。若在咔唑的母体结构上引入不同的功能基团,如:有广泛生物活性的1,3,4-噁二唑,1,3,4-噻二唑,硫脲等生物活性基团,可能增加咔唑类衍生物分子结构上的刚性和稳定性,以期增加这类分子的生物活性和提高其荧光效率和激光量子效率等光学性能。
本文以咔唑为起始原料,设计合成了含有1,3,4-噁二唑,1,3,4-噻二唑,酰基硫脲等活性基团的多个系列的新型咔唑衍生物。
本论文由五章组成:
第一章:咔唑类衍生物的合成、性质及应用进展
对近几年来文献报道的咔唑类新化合物的性质及其应用进行简单综述。
第二章:微波辐射条件下2-芳基-5-(9'-乙基咔唑-3'-基)-1,3,4-噁二唑的合成
在无溶剂条件下,将9-乙基-3-甲酰基咔唑与芳甲酰肼混合均匀,微波辐射下反应首先得到中间体1-(9'-乙基咔唑-3'-亚甲基)-2-芳酰基肼,该中间体用KMnO_4作为氧化剂,DMF为溶剂,在微波辐射条件下,成功地合成了2-芳基-5-(9'-乙基咔唑-3'-基)-1,3,4-噁二唑,该法反应时间短,操作简单,且产率高,而且避免了刺激性、腐蚀性的脱水剂和氧化剂的使用,无环境污染。
第三章:2-芳氨基-5-(9'-乙基咔唑-3'-基)-1,3,4-噻二唑的合成
以9-乙基-3-甲酰基咔唑和4-芳基氨基硫脲为原料,在AcOH催化下,在无水乙醇中合成了1-(9'-乙基咔唑-3'-亚甲基)-4-芳基氨基硫脲,在室温下,该中间体在以MnO_2为氧化剂成功合成了2-芳氨基-5-(9'-乙基咔唑-3'-基)-1,3,4-噻二唑。该法具有反应条件温和,产率高,操作简便的优点。
第四章:含咔唑环二芳酰基硫脲的合成
以9-乙基咔唑为原料,经硝化反应,还原反应,得到了9-乙基-3,6-二氨基咔唑中间体。在室温下,该中间体与芳甲酰基异硫氰酸酯在无水丙酮做溶剂非催化条件下,快捷、高产率合成了含咔唑环二芳酰基硫脲。
第五章:含咔唑环二缩氨基硫脲的合成
以9-乙基咔唑为原料,首先合成9-乙基-3,6-二乙酰基咔唑中间体。然后在磷酸催化下,将其与4-芳基氨基硫脲在无水乙醇中反应,合成了一系列新的含咔唑环二缩氨基硫脲化合物。
以上合成目标化合物的结构都用元素分析、红外光谱及核磁共振氢谱进行了表征,并对相关数据进行了解析。
Carbazole derivatives are widely used to synthesize dyes, pesticides, medicines and resins. Furthermore, carbazole derivatives have been used as non-linear optical material since their excellent optical properties. Carbazole derivatives bearing 1,3,4-oxadiazole, 1,3,4-thiadiazole and thiourea moieties may be good active compounds or optical materials with high fluorescent quantum yields and laser quantum yields.
In this thesis, four series of carbazole derivatives were first synthesized using carbazole as starting material.
This thesis includes five chapters:
Chapter one: The advance of carbazole derivatives in synthesis, properties and applications.
This part were reviewed the advance of new carbazole derivatives and their properties and applications.
Chapter two: Microwave assisted syntheses of 2-aryl-5-(9'-ethylcarbazol -3'-yl)-1,3,4-oxadiazoles
A novel intermediate 1-( 9 -ethyl-9H-carbazole-3 -methylene)-2-aroylhydrazines were prepared by the acid hydrazide and 9-ethyl-3-carbaldehyde under solvent-free condition and micromve irradiation. The intermediate reacted with potassium permanganate in N,N-dimethylformamide under microwave irradiation to form a new family of 1,3,4-oxadiazoles. This synthetic strategy has features of short reaction period, high yield and simple work-up procedure. Furthermore, this eco-friendly strategy efficiently avoids the use of extremely toxic dehydration reagents.
Chapter three: Synthesis of 2-arylamino-5-(9'-ethylcarbazol-3'-yl)-l,3,4-thiadiazoles
N-substituted 9-ethylcarbazol-3-carbaldehyde thiosemicarbazones were first synthesized by the reactions of 9-ethylcarbazol-3-carbaldehyde with various 4-arylthiosemicarbazides in high yield. The 2-arylamino-5-(9'-ethylcarbazol-3'-yl)-1,3,4-thiadiazoles were also obtainted successfully by the cyclization of the novel intermediate N-substituted 9-ethylcarbazol-3-carbaldehyde with MnO_2 at room temperature. This method has advantages of mild reaction condition, high yield and simple work-up procedure.
Chapter four: Synthesis of Novel Carbazole-based Dithioureas
A series of novel carbazole-based dithioureas were efficiently synthesized by reactions of 9-ethyl-3,6-diaminocarbazole with various aroyl isothiocyanates at room temperature under catalyst-free condition in high yield.
Chapter five: Synthesis of Carbazole Based Dithiosemicarbazones
A series of novel carbazole based dithiosemicarbazones were efficiently synthesized by reactions of 3,6-diacetyl-9-ethylcarbazole with various 4-arylthiosemicarbazides in high yield.
The structures of all the compounds were conformed by elemental analyses, IR and ~1H NMR.
本文以咔唑为起始原料,设计合成了含有1,3,4-噁二唑,1,3,4-噻二唑,酰基硫脲等活性基团的多个系列的新型咔唑衍生物。
本论文由五章组成:
第一章:咔唑类衍生物的合成、性质及应用进展
对近几年来文献报道的咔唑类新化合物的性质及其应用进行简单综述。
第二章:微波辐射条件下2-芳基-5-(9'-乙基咔唑-3'-基)-1,3,4-噁二唑的合成
在无溶剂条件下,将9-乙基-3-甲酰基咔唑与芳甲酰肼混合均匀,微波辐射下反应首先得到中间体1-(9'-乙基咔唑-3'-亚甲基)-2-芳酰基肼,该中间体用KMnO_4作为氧化剂,DMF为溶剂,在微波辐射条件下,成功地合成了2-芳基-5-(9'-乙基咔唑-3'-基)-1,3,4-噁二唑,该法反应时间短,操作简单,且产率高,而且避免了刺激性、腐蚀性的脱水剂和氧化剂的使用,无环境污染。
第三章:2-芳氨基-5-(9'-乙基咔唑-3'-基)-1,3,4-噻二唑的合成
以9-乙基-3-甲酰基咔唑和4-芳基氨基硫脲为原料,在AcOH催化下,在无水乙醇中合成了1-(9'-乙基咔唑-3'-亚甲基)-4-芳基氨基硫脲,在室温下,该中间体在以MnO_2为氧化剂成功合成了2-芳氨基-5-(9'-乙基咔唑-3'-基)-1,3,4-噻二唑。该法具有反应条件温和,产率高,操作简便的优点。
第四章:含咔唑环二芳酰基硫脲的合成
以9-乙基咔唑为原料,经硝化反应,还原反应,得到了9-乙基-3,6-二氨基咔唑中间体。在室温下,该中间体与芳甲酰基异硫氰酸酯在无水丙酮做溶剂非催化条件下,快捷、高产率合成了含咔唑环二芳酰基硫脲。
第五章:含咔唑环二缩氨基硫脲的合成
以9-乙基咔唑为原料,首先合成9-乙基-3,6-二乙酰基咔唑中间体。然后在磷酸催化下,将其与4-芳基氨基硫脲在无水乙醇中反应,合成了一系列新的含咔唑环二缩氨基硫脲化合物。
以上合成目标化合物的结构都用元素分析、红外光谱及核磁共振氢谱进行了表征,并对相关数据进行了解析。
Carbazole derivatives are widely used to synthesize dyes, pesticides, medicines and resins. Furthermore, carbazole derivatives have been used as non-linear optical material since their excellent optical properties. Carbazole derivatives bearing 1,3,4-oxadiazole, 1,3,4-thiadiazole and thiourea moieties may be good active compounds or optical materials with high fluorescent quantum yields and laser quantum yields.
In this thesis, four series of carbazole derivatives were first synthesized using carbazole as starting material.
This thesis includes five chapters:
Chapter one: The advance of carbazole derivatives in synthesis, properties and applications.
This part were reviewed the advance of new carbazole derivatives and their properties and applications.
Chapter two: Microwave assisted syntheses of 2-aryl-5-(9'-ethylcarbazol -3'-yl)-1,3,4-oxadiazoles
A novel intermediate 1-( 9 -ethyl-9H-carbazole-3 -methylene)-2-aroylhydrazines were prepared by the acid hydrazide and 9-ethyl-3-carbaldehyde under solvent-free condition and micromve irradiation. The intermediate reacted with potassium permanganate in N,N-dimethylformamide under microwave irradiation to form a new family of 1,3,4-oxadiazoles. This synthetic strategy has features of short reaction period, high yield and simple work-up procedure. Furthermore, this eco-friendly strategy efficiently avoids the use of extremely toxic dehydration reagents.
Chapter three: Synthesis of 2-arylamino-5-(9'-ethylcarbazol-3'-yl)-l,3,4-thiadiazoles
N-substituted 9-ethylcarbazol-3-carbaldehyde thiosemicarbazones were first synthesized by the reactions of 9-ethylcarbazol-3-carbaldehyde with various 4-arylthiosemicarbazides in high yield. The 2-arylamino-5-(9'-ethylcarbazol-3'-yl)-1,3,4-thiadiazoles were also obtainted successfully by the cyclization of the novel intermediate N-substituted 9-ethylcarbazol-3-carbaldehyde with MnO_2 at room temperature. This method has advantages of mild reaction condition, high yield and simple work-up procedure.
Chapter four: Synthesis of Novel Carbazole-based Dithioureas
A series of novel carbazole-based dithioureas were efficiently synthesized by reactions of 9-ethyl-3,6-diaminocarbazole with various aroyl isothiocyanates at room temperature under catalyst-free condition in high yield.
Chapter five: Synthesis of Carbazole Based Dithiosemicarbazones
A series of novel carbazole based dithiosemicarbazones were efficiently synthesized by reactions of 3,6-diacetyl-9-ethylcarbazole with various 4-arylthiosemicarbazides in high yield.
The structures of all the compounds were conformed by elemental analyses, IR and ~1H NMR.
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