CN110240568A - 三取代哒嗪类衍生物及其制备方法 - Google Patents
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- 150000004892 pyridazines Chemical class 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
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- 239000012074 organic phase Substances 0.000 claims description 8
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- 239000003208 petroleum Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
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- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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Abstract
本发明的主要目的在于提供了一种全新的三取代哒嗪类衍生物及其制备方法。该方法实现了由2,5‑二氢‑1,4,5‑硫二氮卓氧化物作为起始原料,以二甲基亚砜(DMSO)作为反应溶剂,80℃反应3小时,便可一步简单高效的合成三取代哒嗪类衍生物,同时提供这类化合物的制备方法。
Description
技术领域
本发明涉及有机合成化学领域,具体是涉及一类三取代哒嗪类衍生物及其制备方法。
背景技术
哒嗪类衍生物骨架结构不仅广泛存在于很多天然有机产物中,而且近些年,哒嗪类衍生物在化学领域、农药和医药领域都已被证明具有很高的潜在应用价值,因此,哒嗪类衍生物的高效合成方法一直是有机化学工作者和药物化学工作者的研究热点之一。目前,哒嗪类衍生物的合成方法虽各有优势,但总体来看,依然存在需要使用金属催化剂,合成步骤繁琐,底物适用范围窄,实验条件苛刻等缺点。因此,研究如何简洁、高效的合成哒嗪类衍生物依然具有十分重要的意义。
发明内容
本发明的主要目的在于提供了一种全新的三取代哒嗪类衍生物及其制备方法。该方法实现了由2,5-二氢-1,4,5-硫二氮卓氧化物作为起始原料,以二甲基亚砜做反应溶剂,80℃反应3小时,便可一步简单高效的合成三取代哒嗪类衍生物,同时提供这类化合物的制备方法。
本发明所述的化合物是Ⅰ所示的化合物—三取代哒嗪类衍生物。
其中:R1为苯基或取代苯基(取代基包含4-甲氧基、4-甲基、4-三氟甲基、4-氟),杂环取代基,烷基取代基,烯基取代基;R2为甲基取代基或乙基取代基。
本发明的三取代哒嗪类衍生物的制备方法如下所示:
目标化合物Ⅰ的制备方法:即将通式Ⅱ所示化合物溶解于二甲基亚砜溶剂中,并加热至80℃反应3小时。将反应混合物冷却至室温,向反应体系中加入一定量的水,并用二氯甲烷萃取三次,合并有机相。用硫酸钠干燥有机相,减压条件下除去有机溶剂,柱层析洗脱得到目标化合物Ⅰ。反应物Ⅱ中:R1为苯基或取代苯基取代基(包含4-甲氧基、4-甲基、4-三氟甲基、4-氟),杂环取代基,烷基取代基,烯基取代基;R2为甲基取代基或乙基取代基。
本发明优选的三取代哒嗪类衍生物的制备方法是,使用二甲基亚砜作为溶剂。
进一步,本发明优选的制备方法是:反应时化合物Ⅱ溶于二甲基亚砜中,溶液浓度为0.1M,即0.1摩尔每升。
更进一步,本发明优选的制备方法在硅胶柱层析时,所用的洗脱液为石油醚与乙酸乙酯的混合溶剂,且体积比V石油醚:V乙酸乙酯=6:1~3:1。
本发明涉及的方法比较新颖,是采用热力学条件下缩环的方法实现三取代哒嗪类衍生物的制备,这一方法文献很少报道。该制备方法除起始原料外,没有用到任何其它试剂,只需要溶剂和热源即可促进反应进行。反应操作简单,后处理方便,产率普遍很高,且在制备过程中无需惰性气体保护。
附图说明
附图1-2为本发明实施例所得到的产物Ⅰ-1的核磁谱图(氢谱和碳谱)
具体实施方式
本发明以下结合具体实施例进行解说。
本发明的制备方法是将化合物Ⅱ溶于有机溶剂中80℃条件下进行反应,反应完成后萃取出粗产品,然后用柱层析方法得到目标化合物。实验表明本发明优选的有机溶剂为二甲基亚砜(DMSO),其反应产物的收率普遍较高,溶液的最优浓度为0.1M。以下是本发明的一个制备化合物最佳实施例。在以下所有实施例中,核磁谱检测通过Varian 300,Bruker400,JEOL 400and Varian 600MHz仪器在CDCl3中获得。δ值为内标相对值(CDCl3定标δ7.261H NMR和77.00 13C NMR)。高分辨质谱(HRMS)通过4G quadrupole time-of-flight(QTof)质谱仪器得到。
实施例1
实施例1的反应式,具体使用的化合物Ⅱ-1以及产物Ⅰ-1的结构如下。
具体实验步骤是:将127mg(0.300mmol,1.0当量)的化合物Ⅱ-1溶于3mL的二甲基亚砜中,将反应体系加热至80℃反应3小时。反应结束后,将反应混合物冷却至室温,向反应体系中加入10mL水,并用10mL二氯甲烷萃取三次,合并有机相。用硫酸钠干燥有机相,减压条件下除去有机溶剂,残留物以200-300目硅胶柱层析洗脱得到目标化合物Ⅰ-1,其产物经过核磁(氢谱、碳谱)、高分辨质谱鉴定,并且Ⅰ-1由单晶进一步确定其结构。
产物Ⅰ-1为黄色固体,产率为76%;熔点:97.1-98.0℃.1H NMR(400MHz,CDCl3)δ8.19(s,1H),8.17–8.11(m,2H),7.58–7.52(m,3H),4.07(s,3H),4.00(s,3H);13C NMR(100MHz,CDCl3)δ165.0,164.5,160.6,149.4,134.4,131.2,129.8,129.2,127.4,122.9,53.6,53.5;ESI-HRMS m/z calcd for C14H12N2O4+H+273.0870,found 273.0869.单晶结构存于剑桥晶体数据库,单晶存储号:CCDC 1885456。
制备本发明的其它化合物(化合物Ⅰ-2至化合物Ⅰ-9)的实施例所用的方法与实施例1相同,反应条件如下:化合物Ⅱ(0.3mmol,1.0当量)溶于3mL的二甲基亚砜中,将反应体系加热至80℃反应3小时。反应结束后,将反应混合物冷却至室温,向反应体系中加入10mL水,并用10mL二氯甲烷萃取三次,合并有机相。用硫酸钠干燥有机相,减压条件下除去有机溶剂,残留物以200-300目硅胶柱层析洗脱得到目标化合物Ⅰ。
各产物结构以及数据表征如下:
产物Ⅰ-2为黄色固体,产率为81%;熔点:102.6-103.3℃.1H NMR(400MHz,CDCl3)δ8.13(d,J=9.2Hz,2H),8.10(s,1H),7.05(d,J=8.8Hz,1H),4.06(s,3H),3.99(s,3H),3.88(s,3H);13C NMR(100MHz,CDCl3)δ165.0,164.8,162.2,160.0,148.6,130.0,129.0,126.8,121.9,114.6,55.4,53.5,53.4;ESI-HRMS m/z calcd for C15H14N2O5+H+303.0975,found303.0975.
产物Ⅰ-3为黄色固体,产率为72%;熔点:88.2-89.0℃.1H NMR(400MHz,CDCl3)δ8.16(s,1H),8.06(d,J=8.0Hz,2H),7.36(d,J=8.0Hz,2H),4.07(s,3H),4.00(s,3H),2.44(s,3H);13C NMR(100MHz,CDCl3)δ165.1,164.7,160.5,149.1,141.8,131.7,130.0,129.9,127.3,122.5,53.6,53.5,21.5;ESI-HRMS m/z calcd for C15H14N2O4+H+287.1026,found287.1025.
产物Ⅰ-4为黄色固体,产率为65%;熔点:85.2-86.2℃.1H NMR(400MHz,CDCl3)δ8.25(d,J=8.4Hz,2H),8.24(s,1H),7.78(d,J=8.4Hz,2H),4.04(s,3H),3.98(s,3H);13CNMR(100MHz,CDCl3)δ164.7,164.1,159.3,150.2,137.8,132.7(q,J=32.6Hz),129.7,127.8,126.1(q,J=3.7Hz),123.6(q,J=270.8Hz),123.3,53.6,53.5;ESI-HRMS m/zcalcd for C15H11F3N2O4+Na+363.0563,found 363.0562.
产物Ⅰ-5为黄色固体,产率为59%;熔点:82.3-82.9℃.1H NMR(400MHz,CDCl3)δ8.18–8.12(m,3H),7.26–7.19(m,2H),4.06(s,3H),3.98(s,3H);13C NMR(100MHz,CDCl3)δ164.9,164.8(d,J=251.1Hz),164.4,159.5,149.4,130.6(d,J=3.1Hz),129.9,129.5(d,J=8.8Hz),122.5,116.4(d,J=21.8Hz),53.6,53.4;ESI-HRMS m/z calcd for C14H11FN2O4+H+291.0776,found 291.774.
产物Ⅰ-6为黄色固体,产率为57%;熔点:149.3-149.6℃.1H NMR(400MHz,CDCl3)δ8.08(s,1H),7.65(d,J=1.2Hz,1H),7.48(d,J=3.6Hz,1H),6.62(dd,J=3.6,1.6Hz,1H),4.03(s,3H),3.97(s,3H);13C NMR(100MHz,CDCl3)δ164.8,164.4,153.2,149.4,148.5,145.8,130.0,120.5,113.1,113.0,53.5,53.4;ESI-HRMS m/z calcd for C12H10N2O5+H+263.0662,found263.0661.
产物Ⅰ-7为黄色油状液体,产率为42%;1H NMR(400MHz,CDCl3)δ7.83(s,1H),4.04(s,3H),3.97(s,3H),1.48(s,9H);13C NMR(100MHz,CDCl3)δ172.4,165.3,164.8,149.1,129.2,122.3,53.4,53.3,37.5,29.8;ESI-HRMS m/z calcd for C12H16N2O4+H+253.1183,found 253.1183.
产物Ⅰ-8为黄色固体,产率为68%;熔点:149.3-149.6℃.1H NMR(400MHz,CDCl3)δ7.93(s,1H),7.80(d,J=16.4Hz,1H),7.62(d,J=6.8Hz,2H),7.46–7.37(m,4H),4.05(s,3H),3.99(s,3H);13C NMR(100MHz,CDCl3)δ164.9,164.6,159.7,148.8,138.0,135.2,129.8,129.7,128.9,127.7,123.5,122.9,53.5,53.4;ESI-HRMS m/z calcd for C16H14N2O4+H+299.1026,found299.1025.
产物Ⅰ-9为黄色固体,产率为74%;熔点:149.3-149.6℃.1H NMR(400MHz,CDCl3)δ8.18(s,1H),8.17–8.10(m,2H),7.58–7.50(m,3H),4.53(q,J=7.2Hz,2H),4.45(q,J=7.2Hz,2H),1.45(t,J=7.2Hz,3H),1.40(t,J=7.2Hz,3H);13C NMR(100MHz,CDCl3)δ164.6,164.1,160.5,150.0,134.7,131.1,129.8,129.2,127.4,122.9,62.9,62.7,14.0,13.9;ESI-HRMS m/z calcd for C16H16N2O4+H+301.1183,found 301.1181.
最后应说明的是:以上所述仅为本发明的优选实施例而已,并不用于限制本发明,尽管参照前述实施例对本发明进行了详细的说明,对于本领域的技术人员来说,其依然可以对前述各实施例所记载的技术方案进行修改,或者对其中部分技术特征进行等同替换。凡在本发明的内容和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (5)
1.三取代哒嗪类衍生物,结构式如下所示,哒嗪骨架结构含有三个取代基,且取代基R1种类多样化。
其中:R1为苯基或取代苯基(取代基包括4-甲氧基、4-甲基、4-三氟甲基、4-氟),杂环取代基,烷基取代基,烯基取代基其中之一;R2为甲基取代基或乙基取代基。
2.权利要求1所述的三取代哒嗪类衍生物,其特征在于,制备方法如下所示:
目标化合物Ⅰ的制备方法:即将通式Ⅱ所示化合物溶解于二甲基亚砜溶剂中,并加热至80℃反应3小时;将反应混合物冷却至室温,向反应体系中加入一定量的水,并用二氯甲烷萃取三次,合并有机相。用硫酸钠干燥有机相,减压条件下除去有机溶剂,柱层析洗脱得到目标化合物Ⅰ。
3.根据权利要求2所述的三取代哒嗪类衍生物的制备方法,其特征在于只使用通式Ⅱ所示化合物作为起始反应原料,以二甲基亚砜作为反应溶剂,80℃条件下反应3小时即可得到目标化合物Ⅰ。
4.根据权利要求3所述的三取代哒嗪类衍生物的制备方法,其特征在于化合物Ⅱ溶于二甲基亚砜中,溶液浓度为0.1M,即0.1摩尔每升,反应即可得到目标化合物Ⅰ。
5.根据权利要求2至4所述的三取代哒嗪类衍生物的制备方法,其特征在于硅胶柱层析所用的洗脱液为石油醚与乙酸乙酯的混合溶剂,且体积比V石油醚:V乙酸乙酯=6:1~3:1即可得到目标化合物Ⅰ。
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