通过烯醇三氟甲磺酸酯和重氮乙酸酯的串联交叉偶联/电环化反应合成取代吡唑。
Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.
机构信息
Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, USA.
出版信息
J Org Chem. 2011 Aug 5;76(15):5915-23. doi: 10.1021/jo201042c. Epub 2011 Jun 27.
Abstract
The synthesis of 3,4,5-trisubstituted pyrazoles via a tandem catalytic cross-coupling/electrocyclization of enol triflates and diazoacetates is presented. The initial scope of this methodology is demonstrated on a range of differentially substituted acyclic and cyclic enol triflates as well as an elaborated set of diazoacetates to provide the corresponding pyrazoles with a high degree of structural complexity.
摘要
通过烯醇三氟甲磺酸酯和重氮乙酸酯的串联催化交叉偶联/电环化反应合成 3,4,5-三取代吡唑。该方法的初始范围通过一系列不同取代的非环和环烯醇三氟甲磺酸酯以及一系列精心设计的重氮乙酸酯进行了证明，以提供具有高度结构复杂性的相应吡唑。
相似文献
1
Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.通过烯醇三氟甲磺酸酯和重氮乙酸酯的串联交叉偶联/电环化反应合成取代吡唑。
J Org Chem. 2011 Aug 5;76(15):5915-23. doi: 10.1021/jo201042c. Epub 2011 Jun 27.
2
Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: efficient synthesis of functionalized 2-pyrazolines.α-烷基重氮乙酸酯的高度对映选择性催化1,3-偶极环加成反应：官能化2-吡唑啉的高效合成
Org Biomol Chem. 2015 Mar 7;13(9):2745-9. doi: 10.1039/c4ob02372b.
3
Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.烯醇重氮乙酸酯与给体-受体取代腙的 vinylogous 反应。取代吡唑衍生物的合成。
J Org Chem. 2013 Feb 15;78(4):1583-8. doi: 10.1021/jo302696y. Epub 2013 Jan 24.
4
When aryldiazonium salts meet vinyl diazoacetates: a cobalt-catalyzed regiospecific synthesis of N-arylpyrazoles.当芳基重氮盐遇到乙烯基重氮乙酸酯时：钴催化的 N-芳基吡唑的区域选择性合成。
Org Lett. 2014 Jun 6;16(11):3110-3. doi: 10.1021/ol5012339. Epub 2014 May 29.
5
A novel synthesis of fluorinated pyrazoles via gold(I)-catalyzed tandem aminofluorination of alkynes in the presence of Selectfluor.通过金（I）催化的炔烃在 Selectfluor 存在下的串联氨氟化反应，合成新型氟化吡唑。
Org Lett. 2011 Aug 19;13(16):4220-3. doi: 10.1021/ol201555z. Epub 2011 Jul 20.
6
Synthesis of imidazo[4,5-c]pyrazoles via copper-catalyzed amidine cyclization.通过铜催化脒环化合成咪唑并[4,5-c]吡唑。
J Org Chem. 2012 Apr 6;77(7):3365-72. doi: 10.1021/jo300176f. Epub 2012 Mar 12.
7
Copper-catalyzed [4 + 1] cycloadditions of alpha,beta-acetylenic ketones with diazoacetates to form trisubstituted furans.铜催化α,β-炔酮与重氮乙酸酯的[4 + 1]环加成反应以形成三取代呋喃。
J Org Chem. 2007 Dec 21;72(26):10276-8. doi: 10.1021/jo7019465. Epub 2007 Nov 28.
8
Regioselective synthesis of 1,3,5-trisubstituted pyrazoles from N-alkylated tosylhydrazones and terminal alkynes.从 N-烷基化的对甲苯磺酰腙和末端炔烃出发，区域选择性合成 1,3,5-三取代吡唑。
Org Lett. 2014 Jan 17;16(2):576-9. doi: 10.1021/ol403447g. Epub 2013 Dec 20.
9
Efficient method for the synthesis of functionalized pyrazoles by catalyst-free one-pot tandem reaction of nitroalkenes with ethyl diazoacetate.无催化剂一锅串联反应合成硝基烯烃与重氮乙酸乙酯的功能化吡唑的有效方法。
Org Biomol Chem. 2009 Nov 7;7(21):4352-4. doi: 10.1039/b915231h. Epub 2009 Aug 28.
10
1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes.2-硫代-3-氯丙烯酰胺与重氮烷烃的 1,3-偶极环加成反应。
Org Biomol Chem. 2010 Jun 21;8(12):2735-48. doi: 10.1039/c002479a. Epub 2010 Apr 23.
引用本文的文献
1
Serendipitous Conversion of an Acetylamino Dideoxy-Octonic Acid Derivate into a Functionalized Carbohydrate-Pyrazole Conjugate and Investigation of the Method´s General Applicability.乙酰氨基二脱氧辛糖酸衍生物意外转化为功能化碳水化合物-吡唑共轭物及该方法的普遍适用性研究。
Molecules. 2024 Oct 15;29(20):4885. doi: 10.3390/molecules29204885.
2
Synthetic Approaches, Biological Activities, and Structure-Activity Relationship of Pyrazolines and Related Derivatives.吡唑啉及相关衍生物的合成方法、生物活性及构效关系。
Top Curr Chem (Cham). 2023 Apr 8;381(3):12. doi: 10.1007/s41061-023-00422-z.
3
Tris(pentafluorophenyl)borane-Catalyzed Carbenium Ion Generation and Autocatalytic Pyrazole Synthesis-A Computational and Experimental Study.三（五氟苯基）硼烷催化碳正离子生成及自催化吡唑合成——一项计算与实验研究
Angew Chem Int Ed Engl. 2021 Nov 8;60(46):24395-24399. doi: 10.1002/anie.202109744. Epub 2021 Oct 12.
4
Substituted Pyrazoles and Their Heteroannulated Analogs-Recent Syntheses and Biological Activities.取代吡唑及其杂环同系物的最新合成及生物活性研究进展。
Molecules. 2021 Aug 18;26(16):4995. doi: 10.3390/molecules26164995.
5
Diazocarbonyl and Related Compounds in the Synthesis of Azoles.二羰基化合物及相关化合物在唑类化合物合成中的应用。
Molecules. 2021 Apr 26;26(9):2530. doi: 10.3390/molecules26092530.
6
Thermal Stability and Explosive Hazard Assessment of Diazo Compounds and Diazo Transfer Reagents.重氮化合物和重氮转移试剂的热稳定性及爆炸危险性评估
Org Process Res Dev. 2020 Jan 17;24(1):67-84. doi: 10.1021/acs.oprd.9b00422. Epub 2019 Nov 28.
7
Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes.通过钯催化末端1,3 - 二烯的1,2 - 氢乙烯基化反应合成高官能化的三取代和四取代烯烃。
J Am Chem Soc. 2015 Jan 21;137(2):608-11. doi: 10.1021/ja511640g. Epub 2015 Jan 6.
8
Total syntheses of (-)-pyrimidoblamic acid and P-3A.(-)-嘧啶并苯并咪唑酸和 P-3A 的全合成。
J Am Chem Soc. 2014 Feb 5;136(5):2119-25. doi: 10.1021/ja412298c. Epub 2014 Jan 21.
9
Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes.钯催化的不对称 β-氢消除反应在制备手性丙二烯中的应用。
J Am Chem Soc. 2013 Apr 3;135(13):4970-3. doi: 10.1021/ja401606e. Epub 2013 Mar 19.
10
Transition metal-mediated synthesis of monocyclic aromatic heterocycles.过渡金属介导的单环芳香杂环化合物的合成。
Chem Rev. 2013 May 8;113(5):3084-213. doi: 10.1021/cr300333u. Epub 2013 Jan 10.
本文引用的文献
1
Tandem 6pi-electrocyclization and cycloaddition of nitrodienes to yield multicyclic nitroso acetals.硝二烯的串联 6π-电环化和环加成反应生成多环硝基亚缩醛。
J Am Chem Soc. 2010 Jul 7;132(26):8876-7. doi: 10.1021/ja1038819.
2
1,3-Dipolar cycloaddition reactions of vinylidenecyclopropane-diesters with aromatic diazomethanes generated in situ.1,3-偶极环加成反应的乙烯基环丙烷二酯与芳香重氮甲烷原位生成。
J Org Chem. 2010 Apr 2;75(7):2296-301. doi: 10.1021/jo100105k.
3
A catalytic asymmetric 6 pi electrocyclization: enantioselective synthesis of 2-pyrazolines.催化不对称6π电环化反应：2-吡唑啉的对映选择性合成
Angew Chem Int Ed Engl. 2009;48(52):9975-8. doi: 10.1002/anie.200905035.
4
Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines.催化不对称6π电环化反应：官能化二氢吲哚的对映选择性合成
Angew Chem Int Ed Engl. 2009;48(52):9979-82. doi: 10.1002/anie.200905169.
5
Identification of N,1,4,4-tetramethyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (PHA-848125), a potent, orally available cyclin dependent kinase inhibitor.鉴定 N,1,4,4-四甲基-8-[[4-(4-甲基哌嗪-1-基)苯基]氨基]-4,5-二氢-1H-吡唑并[4,3-h]喹唑啉-3-甲酰胺（PHA-848125），一种有效的、口服可利用的细胞周期蛋白依赖性激酶抑制剂。
J Med Chem. 2009 Aug 27;52(16):5152-63. doi: 10.1021/jm9006559.
6
Synthesis of fully substituted pyrazoles via regio- and chemoselective metalations.通过区域和化学选择性金属化反应合成全取代吡唑。
Org Lett. 2009 Aug 6;11(15):3326-9. doi: 10.1021/ol901208d.
7
C-H bonds as ubiquitous functionality: a general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition.C-H 键作为普遍存在的功能基：通过 SEM 基团移位实现的区域选择性 C-芳基化和 N-烷基化的顺序反应，为复杂的芳基化吡唑提供了一种通用方法。
J Am Chem Soc. 2009 Mar 4;131(8):3042-8. doi: 10.1021/ja8096114.
8
Design of annulated pyrazoles as inhibitors of HIV-1 reverse transcriptase.作为HIV-1逆转录酶抑制剂的环状吡唑类化合物的设计。
J Med Chem. 2008 Dec 11;51(23):7449-58. doi: 10.1021/jm800527x.
9
Stereoselective synthesis of acetoacetate-derived enol triflates.乙酰乙酸酯衍生的烯醇三氟甲磺酸酯的立体选择性合成。
Org Lett. 2008 Jul 3;10(13):2901-4. doi: 10.1021/ol8010002. Epub 2008 Jun 10.
10
Zinc-catalyzed synthesis of pyrazolines and pyrazoles via hydrohydrazination.锌催化通过氢肼化反应合成吡唑啉和吡唑。
Org Lett. 2008 Jun 19;10(12):2377-9. doi: 10.1021/ol800592s. Epub 2008 May 27.
Zotero 插件