CN114805229B - 1,2,4-三唑的制备 - Google Patents

1,2,4-三唑的制备 Download PDF

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CN114805229B
CN114805229B CN202110100153.3A CN202110100153A CN114805229B CN 114805229 B CN114805229 B CN 114805229B CN 202110100153 A CN202110100153 A CN 202110100153A CN 114805229 B CN114805229 B CN 114805229B
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唐萌
魏泽洋
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Lanzhou University
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    • C07—ORGANIC CHEMISTRY
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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Abstract

本发明属于有机化学领域，涉及1,2,4‑三唑的制备方法。本发明公开3‑氨基‑1,2,4‑三唑和2‑甲苯磺酰基‑1,2,4‑三唑‑3‑酮的制备方法。以苯磺酰腙和氰胺为原料在酸的作用下制备了一系列3‑氨基‑1,2,4‑三唑；以苯磺酰腙和氰酸钾为原料在N‑氯代丁二酰亚胺的作用下制备了一系列2‑甲苯磺酰基‑1,2,4‑三唑‑3‑酮。

Description

1,2,4-三唑的制备
技术领域
本发明属于有机化学领域，涉及1,2,4-三唑的制备方法。
背景技术
近年来，大量研究和实践表明1,2,4-三唑类化合物具有广泛的生物活性，无论在医药领域还是在农药领域1,2,4-三唑类化合物都得到了广泛的应用。
如式一所示，1,2,4-三唑类化合物常用的制备方法为：氯亚甲基酰胺和酰肼通过缩合反应生成N-酰氨基脲，N-酰氨基脲分子内环化缩水生成1,2,4-三唑。该方法主要缺点包括：(1)反应原料氯亚甲基酰胺和酰肼多数商业不可得；(2)反应条件相对苛刻，如氯亚甲基酰胺的制备常使用三氯氧磷(POCl3)，不利于实验操作和工业化生产。
Figure BDA0002908528400000011
本发明以苯磺酰腙和氰胺为原料在酸的作用下制备了一系列3-氨基-1,2,4-三唑，以苯磺酰腙和氰酸钾为原料在N-氯带丁二酰亚胺的作用下制备了一系列2-甲苯磺酰基-1,2,4-三唑-3-酮。该反应原料廉价易得，反应条件温和，底物适用范围广，实验操作简便，更有利于工业化生产。
发明内容
本发明的目的是公开一种3-氨基-1,2,4-三唑的制备方法，其反应通式如式二所示：
Figure BDA0002908528400000012
其中R为：烷基、苯基、取代苯基、苯乙烯基、乙酰乙酯基；
反应所用酸为：三氟化硼、三氯化铁、四氯化钛、三氟甲磺酸钪、三氯化铝、三溴化铝；
反应所用溶剂为：1,2-二氯乙烷、二氯甲烷、氯仿、四氯化碳、乙腈、硝基甲烷、甲苯；
反应所用温度为室温；
反应中苯磺酰腙:氰胺:酸的摩尔比为1:2:1.5。
本发明的另一目的是公开一种2-甲苯磺酰基-1,2,4-三唑-3-酮的制备方法，其反应通式如式三所示：
Figure BDA0002908528400000013
其中R为：烷基、苯基、取代苯基、苯乙烯基、噻吩基；
反应所用溶剂为：乙腈、硝基甲烷、叔丁醇、叔戊醇、异丙醇；
反应所用温度为室温；
反应中苯磺酰腙:氰酸钾:N-氯代丁二酰亚胺的摩尔比为1:2:1.1。
具体实施方式
以下为本发明的实施例，但本发明的内容并不局限于此。
实施例一：3-氨基-1,2,4-三唑的制备方法：
氩气保护下，将苯磺酰腙(0.2mmol)溶于1,2-二氯乙烷(3mL)中，加NH2CN(0.4mmol)，BF3·OEt2(0.3mmol)，室温反应至苯磺酰腙完全消失(5-24小时)，产物乙酸乙酯(200mL)萃取，有机相用饱和Na2CO3溶液洗，食盐水洗，无水MgSO4干燥，减压蒸除溶剂，柱层析分离得3-氨基-1,2,4-三唑。
谱图数据如下：
Figure BDA0002908528400000021
14.9mg,93％yield.1H NMR(400MHz,DMSO-d6)δ＝12.05(brs,1H),7.91-7.88(m,2H),7.42-7.34(m,3H),6.07(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝158.4,157.3,132.3,128.4,128.1,125.3ppm.
Figure BDA0002908528400000022
30.3mg,87％yield.1H NMR(400MHz,DMSO-d6)δ＝11.98(brs,1H),7.78(d,J＝8.4Hz,2H),7.20(d,J＝7.2Hz,2H),6.02(brs,2H),2.32(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝158.4,157.2,137.4,129.0,128.8,125.3,20.9ppm.
Figure BDA0002908528400000023
32.8mg,94％yield.1H NMR(400MHz,DMSO-d6)δ＝12.06(brs,1H),7.84(s,1H),7.23(s,3H),6.01(brs,2H),2.56(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝159.4,156.5,135.8,131.3,130.9,128.6,127.7,125.5,21.9ppm.
Figure BDA0002908528400000024
24.0mg,63％yield.1H NMR(400MHz,DMSO-d6)δ＝11.91(brs,1H),7.83-7.79(m,2H),6.96-6.94(m,2H),6.00(brs,2H),3.77(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝159.3,158.3,157.2,126.7,125.1,113.8,55.1ppm.
Figure BDA0002908528400000025
40.9mg,81％yield.1H NMR(400MHz,DMSO-d6)δ＝12.03(brs,1H),7.92-7.88(m,2H),7.43-7.39(m,2H),7.17-7.07(m,1H),7.05-7.02(m,4H),5.99(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝156.9,156.3,130.06,130.05,127.1,123.6,118.9,118.3ppm；HRMS(ESI):Calcd for C14H13N4O[M+H]+:253.1084,found:253.1092.
Figure BDA0002908528400000031
40.2 mg,75％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.21(brs,1H),7.55(d,J＝8.8 Hz,1H),7.28(d,J＝3.2 Hz,1H),6.90-6.87(m,1H),6.06(brs,2H),3.76(s,3H)；13CNMR(100 MHz,DMSO-d6)δ＝158.3,157.7,156.8,134.5,133.8,116.1,110.9,55.4 ppm；HRMS(ESI):Calcd for C9H10N4OBr[M+H]+:269.0033,found:269.0029.
Figure BDA0002908528400000032
38.3 mg,80％yield.1H NMR(400MHz,DMSO-d6)δ＝12.18(brs,1H),7.74-7.67(m,2H),7.44-7.40(m,1H),7.30-7.27(m,1H),6.09(brs,2H)；13C NMR(100 MHz,DMSO-d6)δ＝158.0,156.7,133.6,133.3,131.3,129.7,127.3,120.6 ppm.
Figure BDA0002908528400000033
35.0 mg,90％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.14(brs,1H),7.92-7.89(m,2H),7.47-7.45(m,2H),6.12(brs,2H)；13C NMR(100 MHz,DMSO-d6)δ＝158.03,157.98,133.2,131.7,129.0,127.5ppm.
Figure BDA0002908528400000034
33.4 mg,86％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.19(brs,1H),7.87-7.83(m,2H),7.46-7.39(m,2H),6.14(brs,2H)；13C NMR(100 MHz,DMSO-d6)δ＝157.5,157.2,134.4,133.2,130.4,127.9,124.9,123.8 ppm.
Figure BDA0002908528400000035
31.1 mg,68％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.28(brs,1H),7.76-7.73(m,1H),7.65-7.63(m,1H),7.41-7.37(m,1H),6.11(brs,2H)；13C NMR(100 MHz,DMSO-d6)δ＝156.8,133.5,132.8,130.2,129.6,129.4,127.8 ppm；HRMS(ESI):Calcd for C8H7N4Cl2[M+H]+:229.0042,found:229.0041.
Figure BDA0002908528400000036
14.0 mg,34％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.28(brs,1H),7.92-7.90(m,1H),7.76-7.73(m,1H),7.69-7.65(m,1H),7.58-7.54(m,1H),6.18(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝157.3,154.7,148.8,131.6,129.4,129.3,124.6,123.1ppm.
Figure BDA0002908528400000041
11.9mg,29％yield.1H NMR(400MHz,DMSO-d6)δ＝12.39(brs,1H),8.26(d,J＝9.2Hz,2H),8.13-8.10(m,2H),6.23(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝157.8,156.8,147.0,138.4,126.1,123.9ppm.
Figure BDA0002908528400000042
14.9mg,40％yield.1H NMR(400MHz,DMSO-d6)δ＝12.02(brs,1H),7.57-7.55(m,2H),7.38-7.23(m,4H),6.92(d,J＝16.4,1H),6.00(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝158.4,157.0,136.5,131.0,128.6,127.8,126.5,119.4ppm；HRMS(ESI):Calcd for C10H11N4[M+H]+:187.0978,found:187.0977.
Figure BDA0002908528400000043
13.2mg,44％yield.1H NMR(400MHz,DMSO-d6)δ＝7.69(d,J＝1.6Hz,1H),6.70(d,J＝3.2Hz,1H),6.55-6.54(m,1H),6.11(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝157.3,151.6,147.3,142.9,111.4,107.9ppm；Calcd for C6H7N4O[M+H]+:151.0614,found:151.0614.
Figure BDA0002908528400000044
10.1mg,36％yield.1H NMR(400MHz,DMSO-d6)δ＝11.88(brs,1H),6.00(brs,2H),1.20(s,9H)；13C NMR(100MHz,DMSO-d6)δ＝164.8,158.1,32.0,29.3ppm；Calcd for C6H13N4[M+H]+:141.1135,found:141.1137.
Figure BDA0002908528400000045
13.2mg,42％yield)1H NMR(400MHz,DMSO-d6)δ＝6.35(brs,2H),4,22(q,J＝7.2Hz,2H),1.25(t,J＝7.2Hz,3H)；Calcd for C5H8N4O2Na[M+Na]+:179.0539,found:179.0541.
实施例二：2-甲苯磺酰基-1,2,4-三唑-3-酮的制备方法：
氩气保护下，将苯磺酰腙(0.2mmol)溶于乙腈(3mL)中，加KOCN(0.4mmol)，NCS(0.22mmol)，室温反应至苯磺酰腙完全消失(5-18小时)，产物乙酸乙酯(200mL)萃取，有机相用饱和Na2CO3溶液洗，食盐水洗，无水MgSO4干燥，减压蒸除溶剂，柱层析分离得2-甲苯磺酰基-1,2,4-三唑-3-酮。
谱图数据如下：
Figure BDA0002908528400000051
43.5 mg,69％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.85(brs,1H),7.93-7.81(m,4H),7.57-7.49(m,5H),2.40(s,3H)；13C NMR(100 MHz,DMSO-d6)δ＝152.3,147.8,145.9,133.9,131.6,130.3,129.1,127.5,125.8,125.1,21.1 ppm；HRMS(ESI):Calcd forC15H14N3O3S[M+H]+:316.0750,found:316.0753.
Figure BDA0002908528400000052
38.2 mg,58％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.53(brs,1H),7.90-7.87(m,2H),7.52-7.48(m,3H),7.45-7.40(m,1H),7.35-7.29(m,2H),2.40(s,6H)；13C NMR(100MHz,DMSO-d6)δ＝152.1,148.6,145.9,137.1,133.9,131.4,130.9,130.3,128.9,127.5,126.2,124.6,21.2,20.6 ppm；HRMS(ESI):Calcd for C16H14N3O3S[M-H]-:328.0761,found:328.0774.
Figure BDA0002908528400000053
42.1mg,61％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.68(brs,1H),7.89-7.87(m,2H),7.76-7.72(m,2H),7.49-7.46(m,2H),7.08-7.05(m,2H),3.80(s,3H),2.38(s,3H)；13CNMR(100 MHz,DMSO-d6)δ＝161.7,152.4,147.7,145.8,134.0,130.2,127.6,127.5,117.3,114.5,55.4,21.1 ppm；HRMS(ESI):Calcdfor C16H14N3O4S[M-H]-:344.0711,found:344.0719.
Figure BDA0002908528400000054
31.5 mg,45％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.90(brs,1H),7.91-7.88(m,2H),7.83-7.82(m,1H),7.78-7.75(m,1H),7.64-7.61(m,1H),7.57-7.47(m,3H),2.39(s,3H)；13C NMR(100 MHz,DMSO-d6)δ＝152.0,146.6,146.0,133.82,133.78,131.3,131.1,130.3,127.6,127.2,125.5,124.5,21.2ppm；HRMS(ESI):Calcd for C15H12N3O3SClNa[M+Na]+:372.0180,found:372.0175.
Figure BDA0002908528400000055
41.7 mg,53％yield.1H NMR(400 MHz,DMSO-d6)δ＝12.66(brs,1H),7.90-7.87(m,2H),7.80-7.78(m,1H),7.61-7.48(m,5H),2.42(s,3H)；13C NMR(100 MHz,DMSO-d6)δ＝151.8,147.9,146.0,133.8,133.4,133.0,131.7,130.3,128.1,127.6,127.1,121.5,21.2ppm；HRMS(ESI):Calcd for C15H11BrN3O3S[M-H]-:391.9710,found:391.9719.
Figure BDA0002908528400000061
30.1mg,43％yield.1H NMR(400MHz,DMSO-d6)δ＝12.90(brs,1H),7.90-7.88(m,2H),7.82-7.80(m,2H),7.61-7.57(m,2H),7.50-7.48(m,2H),2.39(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝152.1,147.0,146.0,136.3,133.8,130.3,129.3,127.63,127.55,124.1,21.2ppm；HRMS(ESI):Calcd for C15H12N3O3SClNa[M+Na]+:372.0180,found:372.0177.
Figure BDA0002908528400000062
44.4mg,65％yield.1H NMR(400MHz,DMSO-d6)δ＝12.57(brs,1H),7.87-7.85(m,2H),7.60-7.57(m,2H),7.50-7.404(m,2H),7.399-7.29(m,4H),6.88(d,J＝16.8Hz,1H),2.39(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝151.8,147.9,145.9,137.6,134.6,133.9,130.3,129.7,129.0,127.5,127.4,113.0,21.1ppm；HRMS(ESI):Calcd for C17H14N3O3S[M-H]-:340.0761,found:340.0771.
Figure BDA0002908528400000063
36.6mg,57％yield.1H NMR(400MHz,DMSO-d6)δ＝12.95(brs,1H),7.90-7.84(m,3H),7.65-7.63(m,1H),7.52-7.49(m,2H),7.23-7.20(m,1H),2.41(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝151.8,146.0,144.2,133.8,130.7,130.3,129.8,128.2,127.5,127.0,21.2ppm；HRMS(ESI):Calcd for C13H10N3O3S2[M-H]-:320.0169,found:320.0169.
Figure BDA0002908528400000064
49.6mg,84％yield.1H NMR(400MHz,DMSO-d6)δ＝12.13(brs,1H),7.83-7.81(m,2H),7.48-7.46(m,2H),2.40(s,3H),1.15(s,9H)；13C NMR(100MHz,DMSO-d6)δ＝157.5,152.6,145.7,134.1,130.0,127.4,32.2,26.9,21.2ppm；HRMS(ESI):Calcd for C13H16N3O3S[M-H]-:294.0918,found:294.0924.
Figure BDA0002908528400000065
43.3mg,63％yield.1H NMR(400MHz,DMSO-d6)δ＝12.12(brs,1H),7.75-7.73(m,2H),7.46-7.44(m,2H),7.25-7.12(m,5H),2.85(t,J＝7.6Hz,2H),2.72-2.69(m,2H),2.41(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝152.1,150.4,145.6,139.7,134.1,130.2,130.1,128.3,127.3,126.2,31.0,27.8,21.1ppm；HRMS(ESI):Calcd for C17H16N3O3S[M-H]-:342.0918,found:342.0927.
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。凡在本发明的精神和原则之内，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 (2)

1.一种3-氨基-1,2,4-三唑的制备方法，其反应通式如式一所示：
Figure FDA0002908528390000011
其中R为：烷基、苯基、取代苯基、苯乙烯基、乙酰乙酯基；
反应所用酸为：三氟化硼、三氯化铁、四氯化钛、三氟甲磺酸钪、三氯化铝、三溴化铝；
反应所用溶剂为：1,2-二氯乙烷、二氯甲烷、氯仿、四氯化碳、乙腈、硝基甲烷、甲苯；
反应所用温度为室温；
反应中苯磺酰腙:氰胺:酸的摩尔比为1:2:1.5。
2.一种2-甲苯磺酰基-1,2,4-三唑-3-酮的制备方法，其反应通式如式二所示：
Figure FDA0002908528390000012
其中R为：烷基、苯基、取代苯基、苯乙烯基、噻吩基；
反应所用溶剂为：乙腈、硝基甲烷、叔丁醇、叔戊醇、异丙醇；
反应所用温度为室温；
反应中苯磺酰腙:氰酸钾:N-氯代丁二酰亚胺的摩尔比为1:2:1.1。
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