<![CDATA[Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF<sub>2</sub>SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines]]>

Teerachai Punirun; Darunee Soorukram; Chutima Kuhakarn; Vichai Reutrakul; Manat Pohmakotr

首页> 外文期刊>The Journal of Organic Chemistry >2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines]]>

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2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines]]>

机译：<！[CDATA [CDATA [四氢异喹啉的氧化二氟甲基化使用TMSCF _{2 SPH：氟化吡咯的合成[2,1- ]异喹啉和苯并[1]苯并[I> A ]喹硫吡啶]]>}

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An efficient C 1-difluoromethylation of tetrahydroisoquinolenes was achieved using TMSCF_(2)SPh as a difluoromethylating agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO~(+)BF_(4)~(–)) as an oxidant. The process provides an access to a variety of C 1-difluoro(phenylsulfanyl)methylated tetrahydroisoquinoline adducts in good yields. These adducts were employed as key precursors for preparing fluorinated pyrrolo[2,1- a ]isoquinoline and benzo[ a ]quinolizidines.

机译：使用TMSCF_（2）SPH以二氟甲基化剂和2,2,6,6-四甲基哌啶-1-氧烷铵四氟硼酸盐（Tempo〜（+）bf_（4）〜（4）〜（ - ））实现了四氢异喹啉的有效C 1-二氟甲基化。作为氧化剂。该方法提供了各种C 1-二氟（苯磺酰基）甲基化四羟基异喹啉加合物的良好产率。这些加合物用作制备氟化吡咯的关键前体[2,1- a]异喹啉和苯并[a]喹硫啉。

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来源
《The Journal of Organic Chemistry》 |2018年第2期|共18页
作者
Teerachai Punirun; Darunee Soorukram; Chutima Kuhakarn; Vichai Reutrakul; Manat Pohmakotr;
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Center of Excellence for Innovation in Chemistry (PERCH?CIC) and Department of Chemistry Faculty of Science Mahidol University Rama VI Road Bangkok 10400 Thailand;

Center of Excellence for Innovation in Chemistry (PERCH?CIC) and Department of Chemistry Faculty of Science Mahidol University Rama VI Road Bangkok 10400 Thailand;

Center of Excellence for Innovation in Chemistry (PERCH?CIC) and Department of Chemistry Faculty of Science Mahidol University Rama VI Road Bangkok 10400 Thailand;

Center of Excellence for Innovation in Chemistry (PERCH?CIC) and Department of Chemistry Faculty of Science Mahidol University Rama VI Road Bangkok 10400 Thailand;

Center of Excellence for Innovation in Chemistry (PERCH?CIC) and Department of Chemistry Faculty of Science Mahidol University Rama VI Road Bangkok 10400 Thailand;

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中图分类有机化学;
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1. 2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines]]> [J] . Teerachai Punirun, Darunee Soorukram, Chutima Kuhakarn, The Journal of Organic Chemistry . 2018,第2期

机译：<！[CDATA [CDATA [四氢异喹啉的氧化二氟甲基化使用TMSCF _{2 SPH：氟化吡咯的合成[2,1- ]异喹啉和苯并[1]苯并[I> A ]喹硫吡啶]]>}
2. The synthesis of 2-nitroaryl-1,2,3,4-tetrahydroisoquinolines, nitro-substituted 5,6-dihydrobenzimidazo(2,1-a)isoquinoline N-oxides and related heterocycles as potential bioreducible substrates for the enzymes NAD(P)H: quinone oxidoreductase 1 and E. coli nitroreductase. [J] . Burke PJ, Wong LC, Jenkins TC, Bioorganic and Medicinal Chemistry Letters . 2011,第24期

机译：2-硝基芳基-1,2,3,4-四氢异喹啉的合成，硝基取代的5,6-二氢苯胺氮（2,1-A）异喹啉N-氧化物和相关杂环作为酶NAD的潜在生物的基质（P） H：醌氧化还原酶1和大肠杆菌硝化酶。
3. Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-a]isoquinolines [J] . Yang Ziqi, Lu Ning, Wei Zhonglin, The Journal of Organic Chemistry . 2016,第23期

机译：取代的3-芳基（杂芳基）-3-氯丙烯醛和四氢异喹啉的碱促进的分子间环化：一种获得吡咯并[2,1-a]异喹啉的方法
4. Some derivatives of benzofuroxan (benzo1,2-c 1,2,5- oxadiazole N-oxide): recent studies on the synthesis and properties [C] . Jonas Sarlauskas Seminar on New Trends in Research of Energetic Materials;NTREM '12 . 2012

机译：苯并呋喃的某些衍生物（苯并1,2-c 1,2,5-恶二唑N-氧化物）：合成与性质的最新研究
5. I. Studies toward the total synthesis of FK-506. II. The alkylation of 2-butyl-4,4-dimethyl-4H-benzo-[d][1,3]-oxathiine-1,1-dioxide, a new class of acyl anion equivalents [D] . Hanson, Susan Marie 2007

机译：I.关于FK-506的全合成的研究。二。一类新的酰基阴离子当量2-丁基-4,4-二甲基-4H-苯并-[d] [1,3]-草硫辛-1,1-二氧化物的烷基化
6. Dimethyl 3-(cyclopropylcarbonyl)pyrrolo[2,1-a]isoquinoline-1,2-dicarboxylate [O] . Honglong Xing, Fan Tang, Wei Wang 2015

机译：3-（环丙基丙基碳烷基）吡咯并[2,1-a]异喹啉-1,2-二羧酸二甲酯
7. Synthesis of Pyrrolo[2,1-a]isoquinolines by Multicomponent 1,3-Dipolar Cycloaddition [O] . Marcel Mirel Popa, Denisa Dumitrescu, Emilian Georgescu, 2013

机译：多组分1,3-偶极环加成反应合成吡咯并[2,1-a]异喹啉
8. Synthesis of Heterocycles: Indolo(2,1-a)isoquinolines, Renewables, and Aptamer Ligands for Cellular Imaging. [R] . Beasley, J. 2013

机译：杂环的合成：用于细胞成像的Indolo（2,1-a）异喹啉，可再生物和适体配体。

2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines]]>

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