CN106631793A - 一种二苯并环庚烷衍生物的制备方法 - Google Patents

一种二苯并环庚烷衍生物的制备方法 Download PDF

Info

Publication number
CN106631793A
CN106631793A CN201610911768.3A CN201610911768A CN106631793A CN 106631793 A CN106631793 A CN 106631793A CN 201610911768 A CN201610911768 A CN 201610911768A CN 106631793 A CN106631793 A CN 106631793A
Authority
CN
China
Prior art keywords
dibenzo
cycloheptane
preparation
alkali
nmr
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610911768.3A
Other languages
English (en)
Other versions
CN106631793B (zh
Inventor
朱钢国
卢丹阳
罗芳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang Normal University CJNU
Original Assignee
Zhejiang Normal University CJNU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang Normal University CJNU filed Critical Zhejiang Normal University CJNU
Priority to CN201610911768.3A priority Critical patent/CN106631793B/zh
Publication of CN106631793A publication Critical patent/CN106631793A/zh
Application granted granted Critical
Publication of CN106631793B publication Critical patent/CN106631793B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明公开了一种二苯并环庚烷衍生物的制备方法，将铜催化剂、碱和配体溶解在有机溶剂中，加入联苯乙炔类化合物和α‑溴代烯丙基丙二酸二乙酯形成反应体系，体系在110℃下反应12小时后，经淬灭、萃取、洗涤、干燥和柱层析处理得到二苯并环庚烷衍生物；该方法扩大了多环稠合环庚烷类化合物的多样性，反应收率良好，具有较大的理论创新价值以及实施价值。

Description

一种二苯并环庚烷衍生物的制备方法
技术领域
本发明属于有机合成领域，具体涉及一种二苯并环庚烷衍生物及其制备方法。
背景技术
秋水仙碱(colchicine)能够与微管蛋白二聚体结合，阻止微管蛋白转换，使细胞停止于有丝分裂中期，从而导致细胞死亡，因此，可以用于地中海热综合征、急性通风等疾病的治疗；而且，它具有很好的抗肿瘤活性，在化疗中具有良好的效果，但是，临床研究表明，秋水仙碱具有较大的毒性不能高剂量的使用。幸运的是，二苯并环庚烷衍生物，包括别秋水仙碱(allocolchicine)、N-acetylcolchinol等许多具有生理活性的药物分子或天然产物，则表现出了比秋水仙碱更强的微管蛋白结合活性和更小的毒副作用(S.Larsson andN.Curr.Top.Med.Chem.,2014,14,274)，是一种更有前景的抗肿瘤候选药物之一，因此，二苯并环庚烷衍生物的合成非常重要。
近几年来，二苯并环庚烷的合成研究愈来愈多，比较典型的方法是利用过渡金属MoCl5/TiCl4、Tl(OCOCF3)3、Pb(OAc)4或PhI(OCOCF3)2催化1,3-二芳基丙烷或1,3-二芳基丙烯氧化二芳基偶联反应合成：
但是，上述反应所用的试剂往往具有较强的毒性或者过量的使用强氧化剂，导致难以用于药物分子的合成或者造成反应的适用范围不够理想。其他的一些合成途径则往往需要较多的反应步骤，导致总产率偏低，合成成本较高。鉴于二苯并环庚烷衍生物的优良药用价值，发展简单、高效的二苯并环庚烷合成路线，开发新的抗癌活性药物分子迫在眉睫。
发明内容
本发明要解决的技术问题是提供了一种反应收率良好，绿色环保且具有良好适用范围的二苯并环庚烷衍生物制备方法。
为解决该技术问题，本发明采用的技术方案为：
一种二苯并环庚烷衍生物的制备方法，其特征在于包括如下步骤：
将铜催化剂、碱和配体溶解在有机溶剂中，加入结构式Ⅱ所示的联苯乙炔类化合物和结构式Ⅲ所示α-溴代烯丙基丙二酸二乙酯形成反应体系，体系在110℃下反应12小时后，经淬灭、萃取、洗涤、干燥和柱层析处理得到结构式I所示的二苯并环庚烷衍生物；
其中，R1为氢、甲基、甲氧基、氟、氯、乙酰基、甲酸甲酯基、三氟甲基、苯基或苯乙炔基。
所述的铜催化剂、碱、配体、结构式Ⅱ所示化合物和结构式Ⅲ所示化合物的摩尔比为0.1：2：0.2：1：1.2。
所述的铜催化剂为六氟磷酸四乙腈铜，所述的碱为碳酸钠，所述的配体为联吡啶，所述有机溶剂为甲苯。
所述的萃取可采用乙酸乙酯作为萃取剂。
所述的洗涤可采用饱和食盐水洗。
所述的柱层析分离的条件为：硅胶300-400目，洗脱液：石油醚/乙酸乙酯的体积比为10/1。
同现有技术相比，本发明具有如下优点：1、首次采用铜催化完成α-溴代烯丙基丙二酸二乙酯与联苯乙炔的环化反应；2、实现了一系列二苯并环庚烷衍生物的合成，底物适用范围广，官能团兼容性好；3、反应操作简单，绿色环保，具有良好应用前景。故本发明具有较大的理论创新价值以及实施价值。
具体实施方式
实施例1
取一支干燥的反应管，称入六氟磷酸四乙腈铜(9.0mg,0.025mmol)、碳酸钠(53.0mg,0.5mmol)、联吡啶(7.8mg,0.05mmol)，然后加入溶于5mL甲苯的联苯乙炔1a(44.5mg,0.25mmol)和α-溴代烯丙基丙二酸二乙酯2a(83.4mg,0.3mmol)。体系在110℃下反应12h后，加10mL水淬灭，用乙酸乙酯(10mL)萃取三次，合并后用饱和食用水洗涤有机相，无水硫酸钠干燥。有机相浓缩后用硅胶(300-400目)柱层析分离(洗脱液：石油醚/乙酸乙酯的体积比为10/1)得到77mg白色固体3aa，熔点86–88℃，收率82％。产物核磁分析1H NMR(600MHz,CDCl3):δ7.46–7.40(m,2H),7.34–7.28(m,4H),7.25–7.21(m,1H),7.18–7.14(m,1H),5.67–5.64(m,1H),4.24–4.17(m,2H),4.09–4.02(m,2H),3.81–3.74(m,1H),3.04–2.98(m,1H),2.75–2.71(m,1H),2.53–2.48(m,1H),2.13–2.07(m,1H),1.27(t,J＝7.1Hz,3H),1.12(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.9,170.5,151.3,140.9,139.7,136.1,135.9,130.3,130.0,128.6,128.5,127.4,127.2,127.0,127.0,125.5,65.3,61.4,61.2,53.9,37.4,35.2,14.0,13.8；HRMS(ESI)calcd for C24H25O4(M+H)+377.1753,found377.1745.
反应式如下：
实施例2
除用结构式1b所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：65％，无色液体。1H NMR(600MHz,CDCl3):δ7.44–7.39(m,2H),7.32–7.26(m,2H),7.21–7.18(m,1H),7.12–7.09(m,1H),6.99–6.96(m,1H),5.68–5.63(m,1H),4.24–4.18(m,2H),4.12–4.04(m,2H),3.79–3.73(m,1H),3.02–2.97(m,1H),2.74–2.70(m,1H),2.49–2.45(m,1H),2.35(s,3H),2.14–2.08(m,1H),1.27(t,J＝7.1Hz,3H),1.14(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ171.0,170.6,151.5,139.7,138.0,136.9,136.0,135.9,131.1,129.9,128.6,128.5,127.7,127.1,127.0,125.3,65.3,61.5,61.2,53.7,37.5,35.2,21.1,14.1,13.9；HRMS(ESI)calcd for C25H27O4(M+H)+391.1909,found 391.1905.
反应式如下：
实施例3
除用结构式1c所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：73％，白色固体，熔点为102–104℃。1H NMR(600MHz,CDCl3):δ7.41–7.38(m,2H),7.30–7.26(m,2H),7.24–7.20(m,1H),6.85–6.81(m,1H),6.74–6.71(m,1H),5.67–5.65(m,1H),4.24–4.18(m,2H),4.12–4.05(m,2H),3.82(s,3H),3.78–3.74(m,1H),3.03–2.98(m,1H),2.76–2.71(m,1H),2.50–2.45(m,1H),2.13–2.07(m,1H),1.27(t,J＝7.1Hz,3H),1.15(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.9,170.5,158.6,151.4,139.4,137.6,135.7,133.5,131.1,128.5,128.4,127.0,126.9,125.2,116.1,111.7,65.2,61.4,61.2,55.2,53.5,37.6,35.4,14.0,13.8；HRMS(ESI)calcd forC25H27O5(M+H)+407.1858,found 407.1850.
反应式如下：
实施例4
除用结构式1d所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：71％，无色液体。1H NMR(600MHz,CDCl3):δ7.44–7.39(m,2H),7.34–7.31(m,1H),7.29–7.26(m,2H),7.01–6.97(m,1H),6.92–6.89(m,1H),5.68–5.65(m,1H),4.25–4.18(m,2H),4.13–4.06(m,2H),3.81–3.73(m,1H),3.02–2.97(m,1H),2.77–2.73(m,1H),2.52–2.46(m,1H),2.10–2.04(m,1H),1.27(t,J＝7.1Hz,3H),1.15(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.8,170.4,161.2(d,J＝246.7Hz),150.9,138.8,138.4(d,J＝7.6Hz),137.0(d,J＝3.1Hz),135.8,131.5(d,J＝8.2Hz),128.6,128.6,127.5,127.1,125.7,117.0(d,J＝21.1Hz),113.7(d,J＝20.9Hz),65.3,61.5,61.3,53.6,37.4,35.2,14.1,13.9；19F NMR(565MHz,CDCl3):δ-115.9；HRMS(ESI)calcd forC24H24O4F(M+H)+395.1659,found 395.1649.
反应式如下：
实施例5
除用结构式1e所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：73％，白色固体，熔点为100–102℃。1H NMR(600MHz,CDCl3):δ7.45–7.39(m,2H),7.36–7.33(m,1H),7.29–7.27(m,2H),7.24–7.21(m,1H),7.19–7.15(m,1H),5.70–5.65(m,1H),4.26–4.18(m,2H),4.15–4.05(m,2H),3.83–3.76(m,1H),3.01–2.95(m,1H),2.79–2.74(m,1H),2.51–2.46(m,1H),2.09–2.03(m,1H),1.27(t,J＝7.1Hz,3H),1.16(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.7,170.3,150.7,139.4,138.5,138.0,135.8,132.7,131.2,130.0,128.6,128.5,127.7,127.1,127.0,125.8,65.2,61.5,61.3,53.6,37.3,35.0,14.0,13.8；HRMS(ESI)calcd for C24H24O4Cl(M+H)+411.1363,found 411.1358.
反应式如下：
实施例6
除用结构式1f所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：70％，白色固体，熔点为111–113℃。1H NMR(600MHz,CDCl3):δ7.92–7.86(m,1H),7.81–7.72(m,1H),7.49–7.44(m,2H),7.41–7.37(m,2H),7.32–7.29(m,1H),5.71–5.67(m,1H),4.26–4.20(m,2H),4.13–4.01(m,2H),3.88–3.77(m,1H),3.07–3.00(m,1H),2.79–2.72(m,1H),2.63(s,3H),2.63–2.59(m,1H),2.10–2.03(m,1H),1.27(t,J＝7.1Hz,3H),1.13(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ198.0,170.7,170.3,150.6,146.1,138.6,136.7,136.0,135.7,130.3,129.9,128.8,128.7,128.3,127.4,127.2,126.2,65.2,61.5,61.3,53.7,37.4,35.2,26.7,14.1,13.9；HRMS(ESI)calcdfor C26H27O5(M+H)+419.1858,found 419.1844.
反应式如下：
实施例7
除用结构式1g所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：70％，白色固体，熔点为96–98℃。1H NMR(600MHz,CDCl3):δ7.99–7.95(m,1H),7.86–7.84(m,1H),7.47–7.44(m,2H),7.38–7.36(m,2H),7.31–7.29(m,1H),5.69–5.67(m,1H),4.24–4.19(m,2H),4.10–4.02(m,2H),3.93(s,3H),3.83–3.79(m,1H),3.05–3.01(m,1H),2.77–2.73(m,1H),2.62–2.59(m,1H),2.05–2.10(m,1H),1.27(t,J＝7.1Hz,3H),1.13(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.7,170.4,167.0,150.7,145.8,138.6,136.4,136.0,131.3,130.1,128.8,128.7,128.6,128.3,128.2,127.2,126.1,65.2,61.5,61.3,53.7,52.1,37.3,35.1,14.0,13.8；HRMS(ESI)calcdfor C26H27O6(M+H)+435.1808,found 435.1804.
反应式如下：
实施例8
除用结构式1h所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：76％，无色液体。1H NMR(600MHz,CDCl3):δ7.57–7.54(m,1H),7.47–7.44(m,2H),7.43–7.37(m,3H),7.32–7.30(m,1H),5.72–5.65(m,1H),4.26–4.18(m,2H),4.11–4.03(m,2H),3.85–3.79(m,1H),3.06–3.02(m,1H),2.82–2.77(m,1H),2.61–2.57(m,1H),2.07–2.01(m,1H),1.28(t,J＝7.1Hz,3H),1.11(t,J＝7.1Hz,3H)；13CNMR(151MHz,CDCl3):δ170.7,170.3,150.3,144.7,138.3,137.1,136.0,130.3,129.1(q,J＝32.3Hz),128.8,128.7,128.3,127.2,126.8(q,J＝4.0Hz),126.2,124.1(q,J＝272.2Hz),123.9(q,J＝4.2Hz),65.3,61.6,61.3,53.7,37.3,35.2,14.0,13.8；19F NMR(565MHz,CDCl3):δ-62.2；HRMS(ESI)calcd for C25H24O4F3(M+H)+445.1627,found445.1624.
反应式如下：
实施例9
除用结构式1i所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：77％，白色固体，熔点为153–155℃。1H NMR(600MHz,CDCl3):δ7.66–7.60(m,2H),7.56–7.52(m,1H),7.51–7.47(m,1H),7.47–7.42(m,3H),7.42–7.32(m,4H),7.32–7.28(m,1H),5.72–5.65(m,1H),4.27–4.17(m,2H),4.10–4.00(m,2H),3.85–3.78(m,1H),3.11–3.02(m,1H),2.79–2.73(m,1H),2.65–2.55(m,1H),2.17–2.10(m,1H),1.27(t,J＝7.1Hz,3H),1.10(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.9,170.5,151.2,140.7,140.0,140.0,139.3,136.6,136.0,130.5,128.9,128.7,128.7,128.6,127.5,127.3,127.1,127.1,125.7,125.6,65.3,61.5,61.2,53.8,37.5,35.5,14.1,13.8；HRMS(ESI)calcd for C30H29O4(M+H)+453.2066,found 453.2062.
反应式如下：
实施例10
除用结构式1j所示的联苯乙炔类化合物代替实施事例1中结构式1a所示的联苯乙炔外，其余操作步骤同实施例1，产率：52％，白色固体，熔点为152–154℃。1H NMR(600MHz,CDCl3):δ7.56–7.54(m,2H),7.48–7.43(m,3H),7.37–7.34(m,5H),7.30–7.28(m,2H),5.70–5.67(m,1H),4.24–4.18(m,2H),4.12–4.04(m,2H),3.83–3.78(m,1H),3.03–2.98(m,1H),2.80–2.73(m,1H),2.56–2.51(m,1H),2.14–2.07(m,1H),1.27(t,J＝7.1Hz,3H),1.15(t,J＝7.1Hz,3H)；13C NMR(151MHz,CDCl3):δ170.8,170.5,150.9,141.2,139.0,136.4,136.0,133.3,131.6,130.3,130.1,128.7,128.6,128.3,128.2,127.8,127.1,125.9,123.3,122.0,89.7,89.4,65.3,61.5,61.3,53.7,37.5,35.1,14.1,13.9；HRMS(ESI)calcd forC32H29O4(M+H)+477.2066,found 477.2043.
反应式如下：

Claims (3)

1.一种二苯并环庚烷衍生物的制备方法，其特征在于包括如下步骤：
将铜催化剂、碱和配体溶解在有机溶剂中，加入结构式Ⅱ所示的联苯乙炔类化合物和结构式Ⅲ所示α-溴代烯丙基丙二酸二乙酯形成反应体系，体系在110℃下反应12小时后，经淬灭、萃取、洗涤、干燥和柱层析处理得到结构式I所示的二苯并环庚烷衍生物；
其中R1为氢、甲基、甲氧基、氟、氯、乙酰基、甲酸甲酯基、三氟甲基、苯基或苯乙炔基。
2.根据权利要求1所述的制备方法，其特征在于，所述的铜催化剂、碱、配体、结构式Ⅱ所示化合物和结构式Ⅲ所示化合物的摩尔比为0.1：2：0.2：1：1.2。
3.根据权利要求1所述的制备方法，其特征在于，所述的铜催化剂为六氟磷酸四乙腈铜，碱为碳酸钠，配体为联吡啶，有机溶剂为甲苯。
CN201610911768.3A 2016-10-19 2016-10-19 一种二苯并环庚烷衍生物的制备方法 Active CN106631793B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610911768.3A CN106631793B (zh) 2016-10-19 2016-10-19 一种二苯并环庚烷衍生物的制备方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610911768.3A CN106631793B (zh) 2016-10-19 2016-10-19 一种二苯并环庚烷衍生物的制备方法

Publications (2)

Publication Number Publication Date
CN106631793A true CN106631793A (zh) 2017-05-10
CN106631793B CN106631793B (zh) 2019-03-08

Family

ID=58855622

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610911768.3A Active CN106631793B (zh) 2016-10-19 2016-10-19 一种二苯并环庚烷衍生物的制备方法

Country Status (1)

Country Link
CN (1) CN106631793B (zh)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1609086A (zh) * 2003-04-14 2005-04-27 弗·哈夫曼-拉罗切有限公司 Mptp亲和标记物
CN101223153A (zh) * 2005-05-12 2008-07-16 默克勒有限公司 二苯并环庚烷化合物和含有这些化合物的药物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1609086A (zh) * 2003-04-14 2005-04-27 弗·哈夫曼-拉罗切有限公司 Mptp亲和标记物
CN101223153A (zh) * 2005-05-12 2008-07-16 默克勒有限公司 二苯并环庚烷化合物和含有这些化合物的药物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TAKASHI NISHIKATA ET AL.: "《An Efficient Generation of a Functionalized Tertiary-Alkyl Radical for Copper-catalyzed Tertiary-Alkylative Mizoroki-Heck type Reaction》", 《J. AM. CHEM. SOC.》 *

Also Published As

Publication number Publication date
CN106631793B (zh) 2019-03-08

Similar Documents

Publication Publication Date Title
CN108047107B (zh) 二苯基二硒醚类化合物的制备方法
CN111690947B (zh) 三氟甲基化芳基酰胺衍生物的电化学合成方法
CN112028809B (zh) 一种3-胺基-4-苯硒基马来酰亚胺化合物的制备方法
CN102702024A (zh) 肟基脱氢枞酸化合物及其合成方法
CN107188832A (zh) 一种利用二氧化碳合成含三氟甲基的氨基甲酸酯的方法
CN109761897B (zh) 一种铜催化N-杂环芳烃类化合物C(sp2)-H键的烷基化的方法
CN113416150A (zh) 一种洛铂中间体的新合成方法
CN106631793B (zh) 一种二苯并环庚烷衍生物的制备方法
CN104892350B (zh) 一种含溴二氟甲基化合物及其制备方法
US20080103316A1 (en) Process for stereoselectively reducing 4-ARYL-4-oxobutanoic acid derivatives
Lin et al. Synthesis of esters from aldehydes or carboxylic acids with dichloromethane, dichloroethane or dichloropropane under mild conditions
Itoh et al. Synthesis of novel bis-and oligo-gem-difluorocyclopropanes
Tantrakarn et al. Synthesis of redox-active biscalix [4] quinones and their electrochemical properties
CN109776409B (zh) 一种利用微通道反应装置合成c-2位多氟官能基团取代喹啉的方法
Zhang et al. Methyltrioxorhenium-catalyzed epoxidation of olefins with hydrogen peroxide as an oxidant and pyridine N-oxide ionic liquids as additives
CN112126941B (zh) 一种多取代10-羟基菲衍生物及其制备方法
CN106810508B (zh) 一种铁催化多组分反应合成苯并[1,4]-氧氮杂卓化合物的方法
Wagh et al. Allylation of 1-phenyl-1-propyne with N-and O-pronucleophiles using polymer supported triphenylphosphine palladium complex as a heterogeneous and recyclable catalyst
CN111138325B (zh) 一种(Z)-β-磺酰基烯胺类化合物的制备方法
CN116041220B (zh) 一种芳基取代的酰胺类化合物的制备方法
CN110407677B (zh) 二苯乙二酮类化合物的制备方法及应用
CN106699491A (zh) 一种基于c‑h活化苯胺类叠氮化制备叠氮类化合物的方法
CN113234061B (zh) 一种双取代螺环芳烃的合成方法
CN111484476B (zh) 3氢-1,2-二硫代2,2-二氧化物及其制备方法
Vardelle et al. An efficient access to new Tröger’s bases using superacidic chemistry

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant