CN114805243B - 1,3,4-噻二唑和1,3,4-硒二唑的制备 - Google Patents

1,3,4-噻二唑和1,3,4-硒二唑的制备 Download PDF

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CN114805243B
CN114805243B CN202110085019.0A CN202110085019A CN114805243B CN 114805243 B CN114805243 B CN 114805243B CN 202110085019 A CN202110085019 A CN 202110085019A CN 114805243 B CN114805243 B CN 114805243B
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唐萌
魏泽洋
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    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • 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
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Abstract

本发明属于有机化学领域，涉及1,3,4‑噻二唑和1,3,4‑硒二唑的制备方法。本发明公开2‑氨基‑1,3,4‑噻二唑和2‑氨基‑1,3,4‑硒二唑的制备方法。以苯磺酰腙和硫氰酸钾为原料在酸和N‑氯代丁二酰亚胺的作用下制备了一系列2‑氨基‑1,3,4‑噻二唑；以苯磺酰腙和硒氰酸钾为原料在酸和N‑氯代丁二酰亚胺的作用下制备了一系列2‑氨基‑1,3,4‑硒二唑。

Description

1,3,4-噻二唑和1,3,4-硒二唑的制备
技术领域
本发明属于有机化学领域，涉及1,3,4-噻二唑和1,3,4-硒二唑的制备方法。
背景技术
近年来，大量研究和实践表明1,3,4-噻二唑和1,3,4-硒二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1,3,4-噻二唑和1,3,4-硒二唑类化合物都得到了广泛的应用。
目前，1,3,4-噻二唑和1,3,4-硒二唑的制备多通过水合肼引入3,4-位氮原子，将异硫氰酸酯、硫氨基脲、异硒氰酸酯、硒氨基脲等作为硫源或硒源使用。如：2016年，Yuanyuan Xie等人报道了以异硒氰酸酯作为硒源和水合肼反应制备硒氨基脲，最终和醛反应制备了2-氨基-1,3,4-硒二唑类化合物(X.Li,B.Gan,T.Xie,P.Yang,Y.Xie,J.Chem.Res.2016,40,178-181；式一)。该类反应主要缺点为：水合肼毒性太高；异硫氰酸酯、硫氨基脲、异硒氰酸酯、硒氨基脲等作为硫源或硒源大部分有浓烈的恶臭气味；且反应条件相对苛刻，不利于实验操作和工业化生产。2019年，Zhaohua Yan等人报道了一种碘促进的以苯磺酰腙和硫氰酸钾为原料制备1,3,4-噻二唑的方法，反应中硫氰酸钾作为一种没有气味的硫源首次被用到1,3,4-噻二唑的制备中(F.Zhu,Z.Yan,C.Ai,Y.Wang,S.Lin,Eur.J.Org.Chem.2019,6561-6565)。但该反应需要在封管中，超过100摄氏度的温度下反应12小时才可完成。封管的使用极大的限制了该反应的应用前景，并且反应底物适用范围有限。
Figure BDA0002908555610000011
本发明以苯磺酰腙和硫氰酸钾为原料在酸和N-氯代丁二酰亚胺的作用下制备了一系列2-氨基-1,3,4-噻二唑；以苯磺酰腙和硒氰酸钾为原料在酸和N-氯代丁二酰亚胺的作用下制备了一系列2-氨基-1,3,4-硒二唑。该反应原料廉价易得，硫氰酸钾和硒氰酸钾分别作为无味低毒的硫源和硒源使用，反应条件温和，实验操作简便；反应底物适用范围广，利用该反应为关键步骤完成了生物活性化合物furidiazine的合成。
发明内容
本发明的目的是公开一种2-氨基-1,3,4-噻二唑的制备方法，其反应通式如式二所示：
Figure BDA0002908555610000012
其中R为：烷基、苯基、取代苯基、呋喃基、噻吩基、吡啶基、乙酰乙酯基；
反应所用酸为：三氟化硼、三氯化铁、三氯化铝、三溴化铝、四氯化钛、异丙醇铝、浓硫酸、浓盐酸；
反应所用溶剂为：叔丁醇、叔戊醇、异戊醇；
反应中苯磺酰腙:硫氰酸钾:酸:N-氯代丁二酰亚胺的摩尔比为1:2:0.5:2；
反应所用温度为回流。
本发明的另一目的是公开一种2-氨基-1,3,4-硒二唑的制备方法，其反应通式如式三所示：
Figure BDA0002908555610000021
其中R为：烷基、苯基、取代苯基、呋喃基、噻吩基、吡啶基、乙酰乙酯基；
反应所用酸为：三氟甲磺酸钪、三氟化硼、三氯化铁、三氯化铝、三溴化铝、溴化锌、浓硫酸、浓盐酸；
反应所用溶剂为：乙腈、叔丁醇、甲醇、乙醇、四氢呋喃；
反应中苯磺酰腙:硒氰酸钾:酸:N-氯代丁二酰亚胺的摩尔比为1:2:0.5:1.1；
反应所用温度为室温。
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。
实施例一：2-氨基-1,3,4-噻二唑的制备方法：
氩气保护下，将苯磺酰腙(0.2mmol)溶于叔丁醇(3mL)中，加KSCN(0.4mmol)，NCS(0.4mmol)，BF3·OEt2(0.1mmol)，回流反应至苯磺酰腙完全消失(0.5-4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-氨基-1,3,4-噻二唑。
谱图数据如下：
Figure BDA0002908555610000022
15.5mg,87％yield.1H NMR(400MHz,DMSO-d6)δ＝7.72-7.70(m,2H),7.45-7.37(m,5H)；13C NMR(100MHz,DMSO-d6)δ＝168.5,156.4,131.0,129.6,129.1,126.3ppm.
Figure BDA0002908555610000023
31.0mg,81％yield.1H NMR(400MHz,DMSO-d6)δ＝7.66-7.63(m,2H),7.40(brs,2H),7.28(d,J＝8.0Hz,2H),2.34(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝168.2,156.5,139.3,129.7,128.3,126.3,20.9ppm.
Figure BDA0002908555610000024
25.3mg,66％yield.1H NMR(400MHz,DMSO-d6)δ＝7.53(d,J＝7.2Hz,1H),7.40-7.27(m,5H),2.48(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝168.8,155.7,135.9,131.4,130.0,129.8,129.1,126.3,21.2ppm.
Figure BDA0002908555610000025
20.3mg,49％yield.1H NMR(400MHz,DMSO-d6)δ＝7.69(dd,J＝6.8,2.0Hz,2H),7.32(brs,2H),7.03(dd,J＝7.2,2.0Hz,2H),3.81(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝167.9,160.3,156.3,127.8,123.6,114.5,55.3ppm.
Figure BDA0002908555610000031
32.9mg,61％yield.1H NMR(400MHz,DMSO-d6)δ＝7.79-7.76(m,2H),7.47-7.41(m,4H),7.23-7.19(m,1H),7.11-7.05(m,4H)；13C NMR(100MHz,DMSO-d6)δ＝168.3,158.0,155.8,130.2,128.2,126.1,124.1,119.3,118.6ppm；HRMS(ESI):Calcd for C14H11N3OSNa[M+Na]+:292.0515,found:292.0509.
Figure BDA0002908555610000032
29.6mg,70％yield.1H NMR(400MHz,DMSO-d6)δ＝7.80-7.77(m,2H),7.55-7.51(m,4H)；13C NMR(100MHz,DMSO-d6)δ＝168.9,155.1,134.0,129.8,129.2,127.9ppm.
Figure BDA0002908555610000033
27.1mg,64％yield.1H NMR(400MHz,DMSO-d6)δ＝7.81-7.80(m,1H),7.73-7.69(m,1H),7.56(brs,2H),7.53-7.48(m,2H)；13C NMR(100MHz,DMSO-d6)δ＝169.1,154.7,133.8,132.9,131.1,129.3,125.4,125.1ppm.
Figure BDA0002908555610000034
35.1mg,83％yield.1H NMR(400MHz,DMSO-d6)δ＝8.02-7.99(m,1H),7.63-7.60(m,1H),7.50-7.46(m,4H)；13C NMR(100MHz,DMSO-d6)δ＝170.1,151.6,131.0,130.5,130.4,130.3,129.6,127.7ppm.
Figure BDA0002908555610000035
19.9mg,51％yield.1H NMR(400MHz,DMSO-d6)δ＝8.12-8.08(m,1H),7.54-7.49(m,3H),7.42-7.32(m,2H)；13C NMR(100MHz,DMSO-d6)δ＝170.0,159.1,156.6,148.5,131.4,131.3,127.7,125.19,125.16,118.8,118.6,116.5,116.2ppm.
Figure BDA0002908555610000036
29.2mg,57％yield.1H NMR(400MHz,DMSO-d6)δ＝7.89-7.87(m,1H),7.78(dd,J＝8.0,1.2Hz,1H),7.53-7.38(m,4H)；13C NMR(100MHz,DMSO-d6)δ＝170.0,153.1,133.8,131.6,131.2,128.1,120.9ppm.
Figure BDA0002908555610000041
30.2mg,68％yield.1H NMR(400MHz,DMSO-d6)δ＝8.28(d,J＝8.8Hz,2H),8.01(d,J＝9.2Hz,2H),7.75(brs,2H)；13C NMR(100MHz,DMSO-d6)δ＝170.0,154.1,147.4,136.8,127.1,124.4ppm.
Figure BDA0002908555610000042
22.1mg,62％yield.1H NMR(400MHz,DMSO-d6)δ＝8.61-8.59(m,1H),8.08-8.05(m,1H),7.929-7.925(m,1H),7.57(brs,2H),7.45-7.42(m,1H)；13C NMR(100MHz,DMSO-d6)δ＝170.1,158.5,149.6,137.4,124.3,119.0ppm.
Figure BDA0002908555610000043
19.4mg,53％yield.1H NMR(400MHz,DMSO-d6)δ＝7.64(dd,J＝4.8,0.8Hz,1H),7.45(brs,2H)7.42(dd,J＝3.6,0.8Hz,1H)7.13(dd,J＝5.2,3.6Hz,1H)；13C NMR(100MHz,DMSO-d6)δ＝168.1,150.6,133.3,128.0,127.6ppm.
Figure BDA0002908555610000044
19.3mg,47％yield.1H NMR(400MHz,DMSO-d6)δ＝7.31-7.18(m,5H),7.02(brs,2H),3.13-3.10(m,2H),2.94(t,J＝7.6Hz,2H)；13C NMR(100MHz,DMSO-d6)δ＝168.3,157.4,140.3,128.5,128.3,126.2,34.6,31.1ppm.
Figure BDA0002908555610000045
23.3mg,74％yield.1H NMR(400MHz,DMSO-d6)δ＝7.01(brs,2H),1.30(s,9H)；13CNMR(100MHz,DMSO-d6)δ＝168.2,167.9,35.5,30.5ppm.
Figure BDA0002908555610000046
18.4mg,53％yield.1H NMR(400MHz,DMSO-d6)δ＝8.01(brs,2H),4.33(q,J＝7.2Hz,2H),1.31(t,J＝7.2Hz,3H)；13C NMR(100MHz,DMSO-d6)δ＝172.4,158.9,147.6,61.8,14.0ppm.
Figure BDA0002908555610000047
26.8mg,63％yield.1H NMR(400MHz,DMSO-d6)δ＝7.91(brs,2H),7.84(d,J＝4.0Hz,1H),7.32(d,J＝4.4Hz,1H)；13C NMR(100MHz,DMSO-d6)δ＝170.1,151.3,147.9,144.5,115.2,111.7ppm；HRMS(ESI):Calcd for C6H5N4O3S[M+H]+:213.0077,found:213.0084
实施例二：2-氨基-1,3,4-硒二唑的制备方法：
氩气保护下，将苯磺酰腙(0.2mmol)溶于乙腈(3mL)中，加KSeCN(0.4mmol)，NCS(0.22mmol)，Sc(OTf)3(0.1mmol)，室温反应至苯磺酰腙完全消失(2-24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2-氨基-1,3,4-硒二唑。
谱图数据如下：
Figure BDA0002908555610000051
26.1mg,58％yield.1H NMR(400MHz,DMSO-d6)δ＝7.73-7.70(m,2H),7.55(brs,2H),7.45-7.40(m,3H)；13C NMR(100MHz,DMSO-d6)δ＝172.2,161.6,133.9,129.4,129.1,127.1ppm；HRMS(ESI):Calcd for C8H8N3Se[M+H]+:225.9878,found:2225.9871.
Figure BDA0002908555610000052
34.2mg,67％yield.1H NMR(400MHz,DMSO-d6)δ＝7.65-7.63(m,2H),7.43(brs,2H),6.99-6.97(m,2H),3.79(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝171.4,161.4,160.2,128.5,126.6,114.4,55.3ppm；HRMS(ESI):Calcd for C9H10N3OSe[M+H]+:255.9984,found:255.9982.
Figure BDA0002908555610000053
29.2mg,61％yield.1H NMR(400MHz,DMSO-d6)δ＝7.51(brs,2H),7.48-7.46(m,1H),7.33-7.31(m,2H),7.29-7.24(m,1H),2.46(s,3H)；13C NMR(100MHz,DMSO-d6)δ＝172.9,160.6,135.5,132.7,131.3,130.6,128.9,126.2,21.3ppm；HRMS(ESI):Calcd forC9H10N3Se[M+H]+:240.0034,found:240.0029.
Figure BDA0002908555610000054
26.1mg,43％yield.1H NMR(400MHz,DMSO-d6)δ＝7.91-7.88(m,1H),7.77-7.75(m,1H),7.58(brs,2H),7.49-7.45(m,1H),7.39-7.34(m,1H)；13C NMR(100MHz,DMSO-d6)δ＝174.3,157.1,134.2,133.7,130.81,130.78,128.0,121.1ppm；HRMS(ESI):Calcd forC8H6N3BrSeNa[M+Na]+:325.8803,found:325.8797.
Figure BDA0002908555610000055
29.1mg,56％yield.1H NMR(400MHz,DMSO-d6)δ＝7.75-7.72(m,2H),7.61(brs,2H),7.50-7.47(m,2H)；13C NMR(100MHz,DMSO-d6)δ＝172.6,160.2,133.8,132.8,129.1,128.6ppm；HRMS(ESI):Calcd for C8H7N3ClSe[M+H]+:259.9488,found:2259.9479.
Figure BDA0002908555610000061
26.6mg,49％yield.1H NMR(400MHz,DMSO-d6)δ＝7.92-7.90(m,1H),7.74-7.63(m,5H)；13C NMR(100MHz,DMSO-d6)δ＝174.1,155.2,147.9,132.5,132.0,130.3,126.3,124.1ppm；HRMS(ESI):Calcd for C8H6N4O2SeNa[M+Na]+:292.9548,found:292.9547.
Figure BDA0002908555610000062
29.0mg,64％yield.1H NMR(400MHz,DMSO-d6)δ＝8.56-8.54(m,1H),8.01-7.98(m,1H),7.90-7.86(m,1H),7.67(brs,2H),7.41-7.38(m,1H)；13C NMR(100MHz,DMSO-d6)δ＝173.4,164.1,151.8,149.7,137.3,124.2,118.5ppm；HRMS(ESI):Calcd for C7H6N4SeNa[M+Na]+:248.9650,found:248.9646.
Figure BDA0002908555610000063
23.3mg,54％yield.1H NMR(400MHz,DMSO-d6)δ＝7.81-7.80(m,1H),7.56(brs,2H),6.92-6.91(m,1H),6.64-6.63(m,1H)；13C NMR(100MHz,DMSO-d6)δ＝171.6,151.0,148.3,144.2,112.4,108.6ppm；HRMS(ESI):Calcd for C6H6N3OSe[M+H]+:215.9671,found:215.9665.
Figure BDA0002908555610000064
21.8mg,47％yield.1H NMR(400MHz,DMSO-d6)δ＝7.60-7.58(m,1H),7.54(brs,2H),7.42-7.41(m,1H),7.11-7.08(m,1H)；13C NMR(100MHz,DMSO-d6)δ＝171.7,154.8,136.5,128.7,127.8,127.4ppm；HRMS(ESI):Calcd for C6H6N3SSe[M+H]+:231.9442,found:231.9438.
Figure BDA0002908555610000065
19.5mg,44％yield.1H NMR(400MHz,DMSO-d6)δ＝8.15(brs,2H),4.29(q,J＝7.2Hz,2H),1.28(t,J＝7.2Hz,3H)；13C NMR(100MHz,DMSO-d6)δ＝176.7,160.8,152.3,61.8,14.1ppm；HRMS(ESI):Calcd for C5H7N3O2SeNa[M+Na]+:243.9596,found:243.9595.
Figure BDA0002908555610000066
19.8mg,39％yield.1H NMR(400MHz,DMSO-d6)δ＝7.31-7.24(m,4H),7.22-7.17(m,1H),7.12(brs,2H),3.13-3.10(m,2H),2.93(t,J＝7.6Hz,2H)；13C NMR(100MHz,DMSO-d6)δ＝172.0,162.9,140.4,128.5,128.3,126.1,35.1,34.3ppm；HRMS(ESI):Calcd forC10H12N3Se[M+H]+:254.0191,found:254.0188.
Figure BDA0002908555610000071
19.3mg,47％yield.1H NMR(400MHz,DMSO-d6)δ＝7.17(brs,2H),1.28(s,9H)；13CNMR(100MHz,DMSO-d6)δ＝174.1,171.9,38.0,31.0ppm；HRMS(ESI):Calcd for C6H12N3Se[M+H]+:206.0191,found:206.0186.
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2-氨基-1,3,4-噻二唑的制备方法，其反应通式如式一所示：
Figure FDA0004184841140000011
其中R为：烷基、苯基、取代苯基、呋喃基、噻吩基、吡啶基、乙氧基甲酰基；
反应所用酸为：三氟化硼、三氯化铁、三氯化铝、三溴化铝、四氯化钛、异丙醇铝、浓硫酸、浓盐酸；
反应所用溶剂为：叔丁醇、叔戊醇、异戊醇；
反应中苯磺酰腙:硫氰酸钾:酸:N-氯代丁二酰亚胺的摩尔比为1:2:0.5:2；
反应所用温度为回流。
2.一种2-氨基-1,3,4-硒二唑的制备方法，其反应通式如式二所示：
Figure FDA0004184841140000012
其中R为：烷基、苯基、取代苯基、呋喃基、噻吩基、吡啶基、乙氧基甲酰基；
反应所用酸为：三氟甲磺酸钪、三氟化硼、三氯化铁、三氯化铝、三溴化铝、溴化锌、浓硫酸、浓盐酸；
反应所用溶剂为：乙腈、叔丁醇、甲醇、乙醇、四氢呋喃；
反应中苯磺酰腙:硒氰酸钾:酸:N-氯代丁二酰亚胺的摩尔比为1:2:0.5:1.1；
反应所用温度为室温。
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Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Acid-Promoted [3 + 1 + 1] Cyclization of N-Tosylhydrazones and Isocyanides: A Method for the Preparation of 4,5-Diaminopyrazoles;Qian Zhang，等;Org. Lett.;第22卷;5182−5186 *
Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N‑Tosylhydrazones;Zeyang Wei,等;Org. Lett.;第23卷;4436−4440 *
I2 Promoted Synthesis of 2-Aminothiadiazoles Employing KSCN as a Sulfur Source Under Metal-Free Conditions;Fuyuan Zhu，等;Eur. J. Org. Chem;6561–6565 *

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