CN109608461A - 一种合成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物的方法 - Google Patents
一种合成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物的方法 Download PDFInfo
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- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title claims abstract description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 22
- -1 quinoxaline compound Chemical class 0.000 title claims abstract description 21
- 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- PCRAJOWHMTYSKR-UHFFFAOYSA-N iodobenzene;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.IC1=CC=CC=C1 PCRAJOWHMTYSKR-UHFFFAOYSA-N 0.000 claims abstract description 9
- KZRAAPTWXAMZHQ-UHFFFAOYSA-N methoxymethanamine Chemical compound COCN KZRAAPTWXAMZHQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- 230000006324 decarbonylation Effects 0.000 claims abstract description 5
- 238000006606 decarbonylation reaction Methods 0.000 claims abstract description 5
- 238000010523 cascade reaction Methods 0.000 claims abstract description 4
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 230000008707 rearrangement Effects 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- 150000003851 azoles Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- WCXDQIODYAEFEZ-UHFFFAOYSA-N C=1C=CN2C=CC=CC12.N1C=CC=CC=C1 Chemical class C=1C=CN2C=CC=CC12.N1C=CC=CC=C1 WCXDQIODYAEFEZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical class ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical class CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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Abstract
一种合成吡啶[1’,2’:1,5]吡唑[3,4‑b]喹喔啉类化合物的方法。以二(三氟乙酸)碘苯作为氧化剂,在室温的条件下,乙腈为溶剂,使邻位同时带有N‑甲氧基甲酰胺基和吡啶基的喹喔啉类化合物发生重排、脱羰和N‑N键偶联串联反应,高产率的生成吡啶[1’,2’:1,5]吡唑[3,4‑b]喹喔啉类化合物。该方法具有操作简单、反应条件温和、官能团兼容性好、区域选择性好和产品产率高等优点。
Description
本发明涉及一种合成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物的方法,具体的说是使用二(三氟乙酸)碘苯作为氧化剂,在室温的条件下,乙腈为溶剂,使邻位同时带有N-甲氧基甲酰胺基和吡啶基的喹喔啉类化合物发生重排、脱羰和N-N键偶联串联反应,高产率的生成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物。该方法具有操作简单、反应条件温和、官能团兼容性好、区域选择性好和产品产率高等优点。
背景技术
吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物是一类非常重要的氮杂吲嗪类衍生物。这类稠杂环类化合物拥有π-共轭体系,在生物学,合成化学和材料科学中具有重要意义,M.Y.Wong and E.Zysman-Colman,Adv.Mater.,2017,29,1605444;M.Bendikov andF.Wudl,Chem.Rev., 2004,104,4891;J.E.Anthony,Chem.Rev.,2006,106,5028;Yu,Y.;Chen,G.;Zhu,L.;Liao,Y.; Wu,Y.;Huang,X.,J.Org.Chem.2016,81,8142。尤其是在荧光材料方面,一些化合物的发色团表现出高度共轭并显示出鲜艳的颜色和强烈的荧光性质,Abet,V.;A.;Mendicuti,F.; Burgos,C.;Alvarez-Builla,J.,J.Org.Chem.2008,73,8800;S.-J.Jung,K.-Y.Kim,J.-M.Hong, S.-J.Eum,J.-D.Lee,J.-H.Jung,M.-J.Kim,Y.-S.No and S.-S.Chung,WO 2015034140A1,2015。
获得这类化合物的关键一般是首先高效的构建吡唑环,Abet,V.;A.;Mendicuti,F.; Burgos,C.;Alvarez-Builla,J.,J.Org.Chem.2008,73,8800,然后再构建分子中的其它环系部分,Vivek Kumar,S.;Ellairaja,S.;Satheesh,V.;SivasamyVasantha,V.;Punniyamurthy,T.,Org. Chem.Front.2018,5,2630。目前,文献调研表明,吡唑环部分的构建主要有两种方法:1)通过过渡金属催化的偶氮/肼类/重氮类或其等效物的环合反应构建吡唑环部分,这类方法的共同特点是吡唑环中的氮源都来自于偶氮/肼类/重氮类或其等效物,Zhu,C.;Feng,C.;Yamane,M., Chem.Commun.2017,53,2606;Li,L.;Wang,H.;Yang,X.;Kong,L.;Wang,F.;Li,X.,J.Org. Chem.2016,81,12038;Yang,J.;Yu,X.;Wu,J.,Synthesis 2014,46,1362;Zhao,J.;Wu,C.;Li,P.; Ai,W.;Chen,H.;Wang,C.;Larock,R.C.;Shi,F.,J.Org.Chem.2011,76,6837;Haag,B.;Peng, Z.;Knochel,P.,Org.Lett.2009,11,4270。2)通过硝基或叠氮芳烃衍生物N-N键偶联反应构建吡唑环部分,这类方法的共同特点是经历了N-N键形成反应得到吡唑环部分,Nykaza,T.V.; Harrison,T.S.;Ghosh,A.;Putnik,R.A.;Radosevich,A.T.,J.Am.Chem.Soc.2017,139,6839; Azad,C.S.;Narula,A.K.,RSC Adv.2015,5,100223;Balog,J.;Riedl,Z.;Hajós,G.,TetrahedronLett.2013,54,5338;Zheng,Q.-Z.;Feng,P.;Liang,Y.-F.;Jiao,N.,Org.Lett.2013,15.4262; Hutchinson.I.;Stevens,M.F.G.,Org.Biomol.Chem.2007,5,114。
虽然上述两种方法可以有效的构建吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物的吡唑环部分,但是,为了进一步扩大氮杂吲嗪类衍生物的化合物库,以适应生物学,合成化学和材料科学的高通量筛选,发展并建立新的合成方法是有机合成化学的重要工作。
发明内容
本发明以邻位同时带有N-甲氧基甲酰胺基和吡啶基的喹喔啉类化合物为原料,二(三氟乙酸)碘苯为氧化剂,乙腈作溶剂,经过一步反应完成了酰胺的重排、脱羰和N-N键偶联串联反应。本发明的目的在于建立一种简单、有效和高选择性的合成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物的方法。为实现上述目的,本发明提供的方法是在室温下进行,通过一步反应,高产率的得到吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物,该方法具有操作简单、反应条件温和、官能团兼容性好、区域选择性好和产品产率高等优点。
本发明采用的技术方案如下:
其中:
反应物为邻位同时带有N-甲氧基甲酰胺基和吡啶基的喹喔啉类化合物;
A选自碳,氮;
取代基R1选自氢,甲基,氯;
取代基R2选自氢,甲基;
反应的促进剂为二(三氟乙酸)碘苯;
反应在乙腈中进行;
反应在室温进行。
综上所述,本发明的方法中,反应步骤仅需一步。反应所使用的二(三氟乙酸)碘苯是易得的化学化工产品;在使用1.1倍量的二(三氟乙酸)碘苯时,反应能达到很好的效果,反应过程简单。在乙腈中,邻位同时带有N-甲氧基甲酰胺基和吡啶基的喹喔啉的原料首先发生重排反应,然后在经过脱羰和N-N键偶联反应得到多并环类化合物吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉。总之,本发明方法条件温和,技术难度低,化学选择性高,产物产率高,反应易于操作。本发明方法反应结束以后只需要将反应混合进行萃取,柱层析提纯即可得到喹唑啉酮类产物。这些优点有利于该发明方法应用于大规模工业化生产。
具体实施方法:
下面通过实例详述本发明。当然,本发明不限于下述的实例。
实例1
向圆底烧瓶(25毫升)中加入1a(56毫克,0.2毫摩尔),二(三氟乙酸)碘苯(94.6毫克,0.22毫摩尔),在2毫升乙腈中,使反应混合物在室温下充分反应(通过TLC监测整个反应过程)。反应完成后,将反应用饱和碳酸氢钠溶液淬灭(10毫升),将混合物用二氯甲烷 (3×5毫升)萃取,合并有机相,然后将有机溶剂真空浓缩,柱层析分离得到红色固体2a(41.8 毫克,95%)。
吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉(2a)
红色固体。熔点:248-250℃;产率:95%,1H NMR(400MHz,CDCl3)δ9.07(d,J=6.8Hz,1H), 8.72(d,J=8.4Hz,1H),8.27(t,J=7.4Hz,2H),7.83(t,J=7.6Hz,1H),7.76-7.68(m,2H),7.63 (t,J=6.8Hz,1H).13C NMR(150MHz,CDCl3)δ152.62,145.51,140.78,134.82,130.88,130.71, 129.72,129.57,129.30,126.96,125.03,121.58,120.04.
吡啶[2,3-b]吡啶[1’,2’:1,5]吡唑[3,4-e]吡嗪(2b)
红色固体。熔点:>300℃;产率:91%,1H NMR(400MHz,CDCl3)δ9.21(dd,J=4.0,2.0Hz, 1H),9.12(d,J=6.4Hz,1H),8.84(d,J=8.4Hz,1H),8.63(dd,J=8.8,2.0Hz,1H),7.86-7.71 (m,3H).13C NMR(150MHz,CDCl3)δ152.67,152.17,147.83,141.23,138.20,135.07,132.84, 129.87,125.96,125.51,122.49,121.09.
2,3-二甲基吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉(2c)
红色固体。熔点:>300℃;产率:87%,1H NMR(600MHz,CDCl3)δ9.04(d,J=6.6Hz,1H), 8.68(d,J=8.4Hz,1H),8.01(s,2H),7.69(t,J=7.5Hz,1H),7.58(t,J=6.6Hz,1H),2.56(d,J= 7.2Hz,6H).13C NMR(100MHz,CDCl3)δ144.81,142.06,140.21,137.95,134.75,129.75, 129.36,128.12,127.87,124.47,123.02,120.84,119.71,20.75,20.40.
2,3-二氯吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉(2d)
红色固体。熔点:>300℃;产率:88%,1H NMR(400MHz,CDCl3)δ9.09(d,J=6.8Hz,1H), 8.72(d,J=8.4Hz,1H),8.40(d,J=9.2Hz,2H),7.81(t,J=7.8Hz,1H),7.70(t,J=7.0Hz,1H). 13C NMR(100MHz,CDCl3)δ144.28,138.99,135.60,132.32,131.87,131.26,130.94,129.89, 129.35,128.85,126.00,122.37,120.43.
8-甲基吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉(2e)
红色固体。熔点:246-248℃;产率:91%,1H NMR(600MHz,CDCl3)δ8.66(d,J=7.8Hz,1H), 8.28(dd,J=20.4,8.4Hz,2H),7.83(t,J=7.5Hz,1H),7.71(q,J=7.0Hz,2H),7.55(d,J=7.2Hz, 1H),3.10(s,3H).13C NMR(100MHz,CDCl3)δ144.52,135.54,131.60,130.51,129.68,129.31, 126.71,124.89,121.50,117.51,117.11,112.90,112.45,18.64。
Claims (1)
1.一种合成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物的方法,以邻位同时带有N-甲氧基甲酰胺基和吡啶基的喹喔啉类化合物为原料,二(三氟乙酸)碘苯为氧化剂,乙腈作溶剂,经过一步反应完成了酰胺的重排、脱羰和N-N键偶联串联反应,合成吡啶[1’,2’:1,5]吡唑[3,4-b]喹喔啉类化合物。
其中:
反应物为邻位同时带有N-甲氧基甲酰胺基和吡啶基的喹喔啉类化合物;
A选自碳,氮;
取代基R1选自氢,甲基,氯;
取代基R2选自氢,甲基;
反应的促进剂为二(三氟乙酸)碘苯;
反应在乙腈中进行;
反应在室温进行。
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CN103342705A (zh) * | 2013-06-17 | 2013-10-09 | 南京工业大学 | 一种合成吡咯[1,2-a]喹喔啉衍生物的方法 |
CN104804009A (zh) * | 2015-04-17 | 2015-07-29 | 河南师范大学 | 一种合成呋喃[2,3-b]喹啉类化合物的方法 |
CN105669668A (zh) * | 2016-03-03 | 2016-06-15 | 上海大学 | 吡啶并吲唑或苯并吡啶并吲唑衍生物及其合成方法 |
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