理解并打断费歇尔吲哚合成反应。
Understanding and Interrupting the Fischer Azaindolization Reaction.
机构信息
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
出版信息
J Am Chem Soc. 2017 Oct 25;139(42):14833-14836. doi: 10.1021/jacs.7b07518. Epub 2017 Oct 12.
Abstract
Experimental and computational studies pertaining to the Fischer azaindolization reaction are reported. These studies explain why pyridylhydrazines are poorly reactive in Fischer indolization reactions, in addition to the origin of hydrazine substituent effects. Additionally, an interrupted variant of Fischer azaindolization methodology is disclosed, which provides a synthetic entryway into fused azaindoline scaffolds.
摘要
报告了与 Fischer 氮茚化反应相关的实验和计算研究。这些研究解释了为什么吡啶基腙在 Fischer 吲哚化反应中反应性差，以及肼取代基效应的起源。此外，还公开了 Fischer 氮茚化方法的中断变体，该变体为融合氮茚骨架提供了合成途径。
相似文献
1
Understanding and Interrupting the Fischer Azaindolization Reaction.理解并打断费歇尔吲哚合成反应。
J Am Chem Soc. 2017 Oct 25;139(42):14833-14836. doi: 10.1021/jacs.7b07518. Epub 2017 Oct 12.
2
Synthesis of Fused Indolines by Interrupted Fischer Indolization in a Microfluidic Reactor.微流控反应器中通过间断费歇尔吲哚合成法合成稠合二氢吲哚
Tetrahedron Lett. 2019 Jan 17;60(3):322-326. doi: 10.1016/j.tetlet.2018.12.045. Epub 2018 Dec 19.
3
An interrupted Fischer indolization approach toward fused indoline-containing natural products.一种用于含稠合二氢吲哚天然产物的间断费歇尔吲哚合成法。
Org Lett. 2009 Aug 6;11(15):3458-61. doi: 10.1021/ol901383j.
4
5
Synthesis of 4- and 6-azaindoles via the Fischer reaction.通过费歇尔反应合成 4-和 6-氮茚。
Org Lett. 2009 Nov 19;11(22):5142-5. doi: 10.1021/ol902139r.
6
Preparation of the isomeric azaindoline family by intramolecular carbolithiation.通过分子内碳锂化反应制备氮杂吲哚异构体家族
Org Lett. 2008 Mar 20;10(6):1071-4. doi: 10.1021/ol702862d. Epub 2008 Feb 14.
7
Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives.伯胺和肼与二卤化物的水相N-杂环化反应：微波辅助合成氮杂环烷烃、异吲哚、吡唑、吡唑烷和酞嗪衍生物。
J Org Chem. 2006 Jan 6;71(1):135-41. doi: 10.1021/jo051878h.
8
A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I.一种通过费歇尔吲哚合成法和烯烃复分解反应构建吲哚咔唑类化合物库的方法：替帕那唑D和I的全合成。
Org Biomol Chem. 2016 Oct 18;14(41):9868-9873. doi: 10.1039/c6ob01679k.
9
Diversity-oriented synthesis of hydrazine-derived compounds from amino isocyanates generated in situ.通过原位生成的氨基异氰酸酯进行肼衍生化合物的多样性导向合成。
Angew Chem Int Ed Engl. 2013 Nov 25;52(48):12705-8. doi: 10.1002/anie.201306379. Epub 2013 Oct 7.
10
Catalytic asymmetric synthesis of [2,3]-fused indoline heterocycles through inverse-electron-demand aza-Diels-Alder reaction of indoles with azoalkenes.通过吲哚与重氮烯烃的逆电子需求氮杂 Diels-Alder 反应，催化不对称合成[2,3]-稠合吲哚杂环。
Angew Chem Int Ed Engl. 2014 Apr 25;53(18):4680-4. doi: 10.1002/anie.201400109. Epub 2014 Mar 25.
引用本文的文献
1
Dearomative logic in natural product total synthesis.天然产物全合成中的非对映选择性逻辑。
Nat Prod Rep. 2022 Dec 14;39(12):2231-2291. doi: 10.1039/d2np00042c.
2
Dual Neutral Sphingomyelinase-2/Acetylcholinesterase Inhibitors for the Treatment of Alzheimer's Disease.双重中性鞘磷脂酶 2/乙酰胆碱酯酶抑制剂治疗阿尔茨海默病。
ACS Chem Biol. 2020 Jun 19;15(6):1671-1684. doi: 10.1021/acschembio.0c00311. Epub 2020 May 14.
3
Synthesis of Fused Indolines by Interrupted Fischer Indolization in a Microfluidic Reactor.微流控反应器中通过间断费歇尔吲哚合成法合成稠合二氢吲哚
Tetrahedron Lett. 2019 Jan 17;60(3):322-326. doi: 10.1016/j.tetlet.2018.12.045. Epub 2018 Dec 19.
4
Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.含甲氧基喹啉里定生物碱的对映选择性全合成及相关研究。
J Am Chem Soc. 2018 May 23;140(20):6483-6492. doi: 10.1021/jacs.8b03404. Epub 2018 May 15.
本文引用的文献
1
Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.抱歉打断一下：对费舍尔经典反应的一种改进，用于杂环和天然产物的合成。
Synlett. 2017;28(1):1-11. doi: 10.1055/s-0036-1588372.
2
Total Synthesis of Scholarisine K and Alstolactine A.学者啡 K 和阿氏乳香脂烷 A 的全合成。
Org Lett. 2017 Apr 7;19(7):1922-1925. doi: 10.1021/acs.orglett.7b00722. Epub 2017 Mar 30.
3
Intramolecular Fischer Indole Synthesis for the Direct Synthesis of 3,4-Fused Tricyclic Indole and Application to the Total Synthesis of (-)-Aurantioclavine.分子内 Fischer 吲哚合成在 3,4-稠合三环吲哚直接合成中的应用及其在（-）-奥替络林全合成中的应用。
Org Lett. 2016 Oct 7;18(19):5098-5101. doi: 10.1021/acs.orglett.6b02541. Epub 2016 Sep 19.
4
Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.阿库铵类生物碱（+）-士的宁、（-）-2（S）-卡他福林和（-）-阿斯皮多菲林A的对映选择性全合成。
J Am Chem Soc. 2016 Feb 3;138(4):1162-5. doi: 10.1021/jacs.5b12880. Epub 2016 Jan 19.
5
Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction.通过可切换级联反应不对称合成四环吡咯并吲哚啉和约束色胺。
Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14133-6. doi: 10.1002/anie.201507041. Epub 2015 Sep 25.
6
The azaindole framework in the design of kinase inhibitors.激酶抑制剂设计中的氮杂吲哚骨架。
Molecules. 2014 Nov 28;19(12):19935-79. doi: 10.3390/molecules191219935.
7
Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach.对映选择性、无保护基全合成薤白生物碱——一种通用方法。
Angew Chem Int Ed Engl. 2015 Jan 2;54(1):315-7. doi: 10.1002/anie.201407280. Epub 2014 Oct 24.
8
Total synthesis of the akuammiline alkaloid picrinine.阿库铵类生物碱苦味林的全合成。
J Am Chem Soc. 2014 Mar 26;136(12):4504-7. doi: 10.1021/ja501780w. Epub 2014 Mar 12.
9
Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.获取阿枯米林生物碱家族：（+）-苦参碱 A 的全合成。
J Am Chem Soc. 2013 Jan 9;135(1):519-28. doi: 10.1021/ja3111626. Epub 2012 Dec 26.
10
Vemurafenib: the first drug approved for BRAF-mutant cancer.威罗菲尼：首个获批准用于 BRAF 突变型癌症的药物。
Nat Rev Drug Discov. 2012 Nov;11(11):873-86. doi: 10.1038/nrd3847. Epub 2012 Oct 12.
Zotero 插件