CN111072588B - 一种含硫氰基噻唑啉类化合物的制备方法 - Google Patents
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明公开了属于有机合成技术领域的一种含硫氰基噻唑啉类化合物的制备方法。所述方法为:向反应器中加入硫代酰胺、硫氰酸铵、溶剂,在通电的作用下反应,反应完毕后,用硅胶柱层析分离得到纯的目标产物。本发明所提供的含硫氰基噻唑啉类化合物的制备方法具有科学合理、条件温和、操作简单、反应时间短等特点。其反应方程式如下:
Description
技术领域
本发明属于有机合成技术领域,具体涉及一种含硫氰基噻唑啉类化合物的制备方法。
背景技术
噻唑啉类化合物作为杂环化合物中重要的一类结构具有广泛的生理活性,经研究表明,此类杂环化合物可以作为谷胱甘肽还原酶抑制剂(Mol.Pharmaceutics 2018,15,3069)、具有抗肿瘤活性(J.Org.Chem.1961,26,3867)以及抗有丝分裂剂(Chem.Rev.2009,109,1371)。同时,硫氰酸酯是一类含有硫氰基官能团的重要化合物,具有多种生物活性,如杀虫(J.Med.Chem.2002,45,3984)、抗微生物(Pharm.Chem.J.2013,47,422)等,在医药和农药等领域有着重要的应用价值,因此,发展一种绿色、高效合成含硫氰基噻唑啉类化合物的新方法具有重要意义。
噻唑啉类化合物的制备方法有:
1)以烯烃、硫代酰胺为原料
Li课题组以烯烃和硫代酰胺为原料,经两步反应制备了噻唑啉类化合物(Org.Lett.2017,19,930)。
2)以苯甲酸、2-氨基乙酸为原料
Seijas课题组以苯甲酸和2-氨基乙酸为原料,加入劳森试剂,在微波高温条件下制备得到噻唑啉类化合物(Tetrahedron.2008,64,9280)。
利用上述方法合成噻唑啉类化合物,具有明显的缺点和不足:1)需要加热;2)操作繁琐;3)反应时间长。
发明内容
为了克服上述现有技术的不足,本发明提供了一种含硫氰基噻唑啉类化合物的制备方法。
一种含硫氰基噻唑啉类化合物的制备方法,所述含硫氰基噻唑啉化合物具有式Ⅰ所示的结构:
式Ⅰ中,其中R1选自苯基、4-甲基苯基、4-甲氧基苯基、4-氯苯基、4-溴苯基、4-三氟甲基苯基、2-噻吩基、2-吡啶基且R2和R3选自氢;R1和R2选自苯基且R3选自H;R1和R3选自苯基且R2选自H;其特征在于,向反应器中加入摩尔比为1:2的硫代酰胺与硫氰酸铵,加入乙腈作为溶剂,在电的作用下,室温下搅拌反应,反应方程式如下:
本发明的有益效果为:本发明提供的含硫氰基噻唑啉类化合物的合成方法科学合理,建立了一种合成多种取代基的含硫氰基噻唑啉类化合物的新方法;该方法具有原料易得、操作简单、反应条件温和、反应时间短等特点。
附图说明
图1为实施例1制备的化合物3a的NMR图谱;
图2为实施例7制备的化合物3g的NMR图谱;
图3为实施例9制备的化合物3i的NMR图谱。
具体实施方式
下面结合附图和具体的实施例对本发明进一步详细的说明:
下述实施例中所述试验方法,如无特殊说明,均为常规方法;所述试剂和材料,如无特殊说明,均可从商业途径获得。
实施例1
含硫氰基噻唑啉化合物3a的制备
向10mL三口瓶中加入N-烯丙基苯并硫代酰胺1a(0.2mmol,36mg),硫氰酸铵2(0.4mmol,30mg)和乙腈(4mL)。两根石墨棒(Φ5mm)分别作为阳极和阴极。将反应混合物在2V的恒定电压下室温搅拌5小时。反应完成后,用旋转蒸发仪除去溶剂。通过硅胶快速色谱法,使用石油醚和乙酸乙酯作为洗脱液,得到产物3a,产率84%。
谱图解析数据3a:
1H NMR(CDCl3,500MHz):δ7.85–7.78(m,2H),7.46(m,3H),4.64(dd,J=16.4,2.2,1H),4.41(dd,J=16.5,7.8,1H),4.27–4.18(m,1H),3.16(dd,J=13.4,6.5,1H),3.05(dd,J=13.4,8.2,1H).13C NMR(CDCl3,125MHz):δ166.8,132.6,131.7,128.7,128.4,111.3,68.5,50.1,38.9.HRMS(ESI-TOF,[M+H+]):calcd for C11H11N2S2,235.0364,found235.0369.
实施例2
用1b代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3b:
1H NMR(CDCl3,500MHz):δ7.79–7.59(m,2H),7.23(d,J=7.9,2H),4.62(dd,J=16.4,2.1,1H),4.39(dd,J=16.4,7.8,1H),4.20(m,1H),3.15(dd,J=13.4,6.5,1H),3.04(dd,J=13.4,8.2,1H),2.40(s,3H).13C NMR(CDCl3,125MHz):δ166.7,142.2,129.9,129.4,128.4,111.4,68.4,49.9,38.9,21.5.HRMS(ESI-TOF,[M+H+]):calcd for C12H13N2S2,249.0520,found 249.0524.
实施例3
用1c代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3c:
1H NMR(CDCl3,500MHz):δ7.80–7.74(m,2H),6.96–6.90(m,2H),4.60(dd,J=16.3,2.1,1H),4.37(dd,J=16.2,7.7,1H),4.20(m,1H),3.85(s,3H),3.16(dd,J=13.4,6.5,1H),3.04(dd,J=13.4,8.2,1H).13C NMR(CDCl3,125MHz):δ166.0,162.3,130.1,125.3,114.0,111.3,68.3,55.4,50.1.HRMS(ESI-TOF,[M+H+]):calcd for C12H13N2OS2,265.0469,found 265.0475.
实施例4
用1d代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3d:
1H NMR(CDCl3,500MHz):δ7.75(d,J=8.4,2H),7.40(d,J=8.4,2H),4.63(dd,J=16.5,2.1,1H),4.40(dd,J=16.5,7.9,1H),4.29–4.21(m,1H),3.16(dd,J=13.4,6.5,1H),3.05(dd,J=13.4,8.1,1H).13C NMR(CDCl3,125MHz):δ165.6,137.8,131.0,129.7,128.9,111.2,68.5,50.4,38.8.HRMS(ESI-TOF,[M+H+]):calcd for C11H10N2S2Cl,268.9974,found268.9977.
实施例5
用1e代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3e:
1H NMR(CDCl3,500MHz):δ7.81–7.71(m,2H),7.66–7.56(m,2H),4.69(dd,J=16.5,2.2,1H),4.46(dd,J=16.6,7.9,1H),4.32(m,1H),3.23(dd,J=13.4,6.5,1H),3.12(dd,J=13.5,8.1,1H).13C NMR(CDCl3,125MHz):δ165.7,131.9,131.5,129.8,126.3,111.1,68.5,50.4,38.8.HRMS(ESI-TOF,[M+H+]):calcd for C11H10N2S2Br,312.9469,found312.9474.
实施例6
用1f代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3f:
1H NMR(CDCl3,500MHz):δ7.93(d,J=8.1,2H),7.69(d,J=8.2,2H),4.67(dd,J=16.7,2.3,1H),4.45(dd,J=16.7,7.9,1H),4.30(m,1H),3.18(dd,J=13.5,6.6,1H),3.07(dd,J=13.5,8.0,1H).13C NMR(CDCl3,125MHz):δ165.5,135.7,133.2(q,J=32.9),128.7,125.6,125.6,123.6(q,J=272.6),111.1,68.7,50.5,38.8.HRMS(ESI-TOF,[M+H+]):calcdfor C12H10N2F3S2,303.0237,found 303.0244.
实施例7
用1g代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3g:
1H NMR(CDCl3,500MHz):δ7.51(dd,J=5.2,1.1,1H),7.45(dd,J=3.8,1.1,1H),7.11(dd,J=5.1,3.7,1H),4.59(dd,J=16.3,2.0,1H),4.38(dd,J=16.3,7.6,1H),4.27(m,1H),3.18(dd,J=13.4,6.6,1H),3.08(dd,J=13.4,8.1,1H).13C NMR(CDCl3,125MHz):δ159.9,136.2,131.3,130.5,127.7,111.2,67.9,51.0,38.7.HRMS(ESI-TOF,[M+H+]):calcdfor C9H9N2S2,240.9928,found 240.9931.
实施例8
用1h代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3h:
1H NMR(CDCl3,500MHz):δ8.64(m,1H),8.05(dd,J=7.9,1.2,1H),7.78(m,1H),7.38(m,1H),4.71(dd,J=16.9,2.3,1H),4.49(dd,J=16.9,8.1,1H),4.16(m,1H),3.18(dd,J=13.4,6.3,1H),3.04(dd,J=13.4,8.4,1H).13C NMR(CDCl3,125MHz):δ169.4,150.5,149.4,136.7,125.8,121.6,111.4,68.9,48.5,39.0.HRMS(ESI-TOF,[M+Na+]):calcd for C10H9N3NaS2,258.0136,found 258.0139.
实施例9
用1i代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3i:
1H NMR(CDCl3,500MHz):δ7.82–7.76(m,2H),7.55–7.51(m,1H),7.50–7.42(m,7H),4.91(dd,J=16.3,3.6,1H),4.79(ddd,J=10.7,8.1,3.6,1H),4.68(dd,J=16.3,8.1,1H),4.36(d,J=10.5,1H).13C NMR(CDCl3,125MHz):δ137.8,132.5,131.6,129.4,129.2,128.6,128.3,127.7,110.2,68.4,56.5,54.6.HRMS(ESI-TOF,[M+H+]):calcd for C17H15N2S2,311.0677,found 311.0680.
实施例10
用1j代替实例1中的1a,其他条件同实例1,实验结果见表1。
谱图解析数据3j:
1H NMR(CDCl3,500MHz):δ7.89–7.77(m,2H),7.51(t,J=7.4,1H),7.48–7.41(m,4H),7.41–7.35(m,3H),4.92(d,J=16.1,1H),4.56(d,J=16.1,1H),3.67(m,2H).13C NMR(CDCl3,125MHz):δ167.4,138.8,132.7,131.8,129.2,128.7,128.6,128.3,127.1,111.6,73.4,69.3,46.9.HRMS(ESI-TOF,[M+H+]):calcd for C17H15N2S2,311.0677,found311.0683.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4404070A (en) * | 1982-07-23 | 1983-09-13 | Celanese Corporation | Electrochemical production of 2,6-diaminobenzobisthiazole |
JPS63211285A (ja) * | 1987-02-27 | 1988-09-02 | Taiho Yakuhin Kogyo Kk | 2β−置換メチルペニシリン誘導体の製造法 |
CN103741163A (zh) * | 2013-12-20 | 2014-04-23 | 哈尔滨理工大学 | 一种2-氯-5-氯甲基-1,3-噻唑的合成方法 |
CN109338402A (zh) * | 2018-11-29 | 2019-02-15 | 福建医科大学 | 一种水中电催化苯并硫代酰胺类化合物合成苯并噻唑的方法 |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4404070A (en) * | 1982-07-23 | 1983-09-13 | Celanese Corporation | Electrochemical production of 2,6-diaminobenzobisthiazole |
JPS63211285A (ja) * | 1987-02-27 | 1988-09-02 | Taiho Yakuhin Kogyo Kk | 2β−置換メチルペニシリン誘導体の製造法 |
CN103741163A (zh) * | 2013-12-20 | 2014-04-23 | 哈尔滨理工大学 | 一种2-氯-5-氯甲基-1,3-噻唑的合成方法 |
CN109338402A (zh) * | 2018-11-29 | 2019-02-15 | 福建医科大学 | 一种水中电催化苯并硫代酰胺类化合物合成苯并噻唑的方法 |
Non-Patent Citations (3)
Title |
---|
Access to SCN-containing thiazolines via electrochemical regioselective thiocyanothiocyclization of N-allylthioamides;Yan-An Zhang等;《Org. Chem. Front.》;20200409;第7卷;第1321-1326页 * |
Qumruddeen等.Lewis Base/Brønsted Acid Cocatalysis for Thiocyanation of Amides and Thioamides.《J. Org. Chem.》.2020,第85卷 * |
Transition-Metal-Free Tandem Radical Thiocyanooxygenation of Olefinic Amides: A New Route to SCN-Containing Heterocycles;Hua Yang等;《Org. Lett.》;20150403;第17卷;第1998-2001页 * |
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