Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes

Science, Journal Year: 2021, Volume and Issue: 371(6536), P. 1338 - 1345

Published: March 25, 2021

Heteroaromatics lured into cycloadditions The Diels-Alder reaction is widely used to produce six-membered carbon rings from alkenes and dienes. such as quinolines resemble dienes in principle, but practice their pairs of double bonds are inert toward because aromatic stabilization. Ma et al. report that by using an iridium photosensitizer, they could excite related azaarenes triplet states, thereby disrupting the aromaticity enabling intermolecular, Diels-Alder–like reactivity (see Perspective Schmidt). reactions proceeded exclusively at flanking carbons outside nitrogen-containing ring. Science , this issue p. 1338 ; see also 1313

Language: Английский

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Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(3), P. 1122 - 1246

Published: Jan. 2, 2024

Dearomatization reactions have become fundamental chemical transformations in organic synthesis since they allow for the generation of three-dimensional complexity from two-dimensional precursors, bridging arene feedstocks with alicyclic structures. When those processes are applied to pyridines, quinolines, and isoquinolines, partially or fully saturated nitrogen heterocycles formed, which among most significant structural components pharmaceuticals natural products. The inherent challenge lies low reactivity heteroaromatic substrates, makes dearomatization process thermodynamically unfavorable. Usually, connecting event irreversible formation a strong C–C, C–H, C–heteroatom bond compensates energy required disrupt aromaticity. This aromaticity breakup normally results 1,2- 1,4-functionalization heterocycle. Moreover, combination these subsequent tandem stepwise protocols allows multiple heterocycle functionalizations, giving access complex molecular skeletons. aim this review, covers period 2016 2022, is update state art nucleophilic dearomatizations showing extraordinary ability dearomative methodology indicating their limitations future trends.

Language: Английский

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Sequential and direct multicomponent reaction (MCR)-based dearomatization strategies

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 49(23), P. 8721 - 8748

Published: Jan. 1, 2020

This review focuses on the comprehensive understanding of different multicomponent reaction (MCR) cascades involving dearomatization as characteristic step.

Language: Английский

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Tridentate ONO hydrazone Schiff base complexes in organic transformations: Catalytic and mechanistic studies

Inorganica Chimica Acta, Journal Year: 2023, Volume and Issue: 560, P. 121835 - 121835

Published: Oct. 28, 2023

Language: Английский

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Recent advances in catalytic enantioselective multicomponent reactions

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(39), P. 7751 - 7773

Published: Jan. 1, 2020

Multicomponent reactions have demonstrated a remarkable impact on the synthesis of complex compounds, with high atom economy. In this review, last decade contributions to enantioselective MCRs by focusing catalytic approaches are discussed.

Language: Английский

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Transition metal catalyzed asymmetric multicomponent reactions of unsaturated compounds using organoboron reagents

Chemical Communications, Journal Year: 2020, Volume and Issue: 57(4), P. 441 - 459

Published: Dec. 10, 2020

Transition metal-catalyzed asymmetric multicomponent reactions using organoboron compounds have been utilized extensively for C–B, C–C, and other bond-forming reactions. This feature article highlights the important discoveries in this topic.

Language: Английский

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Catalytic Enantioselective Isocyanide‐Based Reactions: Beyond Passerini and Ugi Multicomponent Reactions

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 27(22), P. 6598 - 6619

Published: Sept. 23, 2020

Abstract The development of catalytic enantioselective isocyanide‐based reactions is currently great interest because the resulting products are valuable in organic synthesis, pharmacological chemistry, and materials science. This review assembles comprehensively summarizes recent achievements this rapidly growing area according to reaction types. Special attention paid advantages, limitations, possible mechanisms, synthetic applications each reaction. In addition, a personal outlook on opportunities for further exploration given at end.

Language: Английский

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Cobalt-Catalyzed Asymmetric Dearomative [3 + 2] Annulation of Quinolines, Isoquinolines, and Pyridines

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(17), P. 11528 - 11540

Published: Aug. 16, 2023

A highly enantioselective dearomative [3 + 2] annulation of quinolines, isoquinolines, and pyridines with donor–acceptor aminocyclopropanes was achieved. With C1-symmetric imidazoline-pyrroloimidazolone pyridine as the tridentate ligand Co(OTf)2 Lewis acid, diverse chiral indolizidine benzo-fused derivatives were obtained in good yields (up to 98% yield), excellent diastereoselectivities (>20:1 dr), enantioselectivities ee). Mechanistic experiments density functional theory (DFT) calculations revealed that nitrogen acted a bifunctional ligand. The not only coordinated Co(II) salt activate aminocyclopropane via bidentate coordination, but also formed H-bond oxygen atom succinimide moiety fix orientation aminocyclopropane, thus facilitating nucleophilic attack N-heteroaromatics. Additionally, high enantioselectivity reaction governed by steric factors.

Language: Английский

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Novel magnetic propylsulfonic acid-anchored isocyanurate-based periodic mesoporous organosilica (Iron oxide@PMO-ICS-PrSO3H) as a highly efficient and reusable nanoreactor for the sustainable synthesis of imidazopyrimidine derivatives

Scientific Reports, Journal Year: 2020, Volume and Issue: 10(1)

Published: June 30, 2020

Abstract In this study, preparation and characterization of a new magnetic propylsulfonic acid-anchored isocyanurate bridging periodic mesoporous organosilica (Iron oxide@PMO-ICS-PrSO 3 H) is described. The iron H nanomaterials were characterized by Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy field emission scanning electron microscopy as well thermogravimetric analysis, N 2 adsorption–desorption isotherms vibrating sample magnetometer techniques. Indeed, the obtained materials are first example thermally stable isocyanurate-based solid acid. Furthermore, catalytic activity Iron nanomaterials, novel highly efficient recoverable nanoreactor, was investigated for sustainable heteroannulation synthesis imidazopyrimidine derivatives through Traube–Schwarz multicomponent reaction 2-aminobenzoimidazole, C‒H acids diverse aromatic aldehydes. advantages green protocol low catalyst loading, high to quantitative yields, short times recyclability at least four consecutive runs.

Language: Английский

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Synthesis of Dihydroisoquinoline and Dihydropyridine Derivatives via Asymmetric Dearomative Three-Component Reaction

CCS Chemistry, Journal Year: 2021, Volume and Issue: 4(6), P. 2000 - 2008

Published: June 9, 2021

Open AccessCCS ChemistryRESEARCH ARTICLE6 Jun 2022Synthesis of Dihydroisoquinoline and Dihydropyridine Derivatives via Asymmetric Dearomative Three-Component Reaction Guihua Pan, Changli He, Min Chen, Qian Xiong, Weidi Cao Xiaoming Feng Pan Key Laboratory Green Chemistry Technology, Ministry Education, College Chemistry, Sichuan University, Chengdu 610064 , He Chen Xiong *Corresponding authors: E-mail Address: [email protected] https://doi.org/10.31635/ccschem.021.202101060 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail We report the first asymmetric three-component nucleophilic addition/dearomative [4+2] cycloaddition/isomerization cascade transient dipoles generated from N-heteroarenes allenoates with methyleneindolinones in presence chiral N,N′-dioxide/metal complexes. This tandem reaction enabled rapid access versatile polycyclic N-heterocycles good excellent enantioselectivities under mild conditions spite strong background reaction, including 1,2-dihydroisoquinoline, 1,2-dihydropyridine derivatives, others. Meanwhile, a series control experiments were conducted elucidate mechanism roles additives. Download figure PowerPoint Introduction Nitrogen-containing heterocyclic compounds represent largest most diverse family organic compounds, which play crucial role numerous pharmaceuticals agrochemicals.1–4 A recent analysis U.S. Food Drug Administration (U.S. FDA) approved drugs reveals that 59% small-molecule contain at least one N-heterocycle.2 As significant subset such hydroisoquinoline hydropyridine motifs are particularly interesting.1 For instance, skeletons prevalent bioactive alkaloids drug molecules, as crystamidine ( A), jamtine B), haiderine C), emetine D) (Scheme 1a).5–11 Note also hydropyridines useful synthetic intermediates for synthesis complex nitrogenous natural products pharmaceutical targets12–15 exemplified by practical influenza (–)-oseltamivir (Tamiflu, E).13 Therefore, development expeditious entries especially enantioenriched ones containing peripheral functional groups, would make great contribution discovery new molecules or drugs. Scheme 1 | (a b) Representative biologically active N-heterocyclic catalytic dearomative reaction. Dearomatization strategy multicomponent fashion represents efficient methods construction natural-product-like structures,16–21 can easily achieve extended molecular complexity diversity simple starting materials high atomic economy. Huisgen 1,4-dipoles heteroarenes (such pyridine, quinolone, isoquinoline) electrophilic π-systems acetylenic esters, allenoates, diazoesters) broadly explored topic dearomatization chemistry (poly)cyclic N-heterocycles.22–26 Among these activated π-systems, allenoates27–29 an important reagent have been less explored. Only Nair's30,31 Shi's32 groups reported reactions isoquinoline, allenoate, α,β-unsaturated compound ketone, respectively. key 1,4-dipole was involved through addition isoquinoline 1,3-diester substituted allene, subsequently intercepted trapping component cycloaddition, affording derivatives low moderate yields diastereoselectivities. To best our knowledge, enantioselective version this field is still challenge, may be attributed highly reactive short-lived zwitterions, giving rise difficulty stereocontrol.33–35 Inspired performance N,N′-dioxide-based Lewis acid catalysts showed activation stereocontrol methyleneindolinone bidentate coordination,36–39 we proposed stereoselective sequential involving allenoate could realized careful choice type ligand metal salt. Herein, present N-heteroarenes, N,N′-dioxide-Mg(II) complexes 1b). The bicyclic aromatic (isoquinoline, quinoline, phthalazine, phenanthridine), successfully varied, well more challenging monocyclic pyridine because its increased resonance stabilization possibility poisoning system.20,26 result, wide range afforded results conditions. Experimental Methods General procedure 2a oven-dried tube added Mg(OTf)2 (3.2 mg, 0.01 mmol, 10 mol %), L3-Pi c H (4.9 1b (33.1 0.10 mmol) N2 atmosphere. Tetrahydrofuran (THF; 0.5 mL) added, mixture stirred 35 °C 30 min. Then concentrated vacuo, CH2Cl2 (1.0 H2O (0.5 μL) added. Subsequently, (12.9 3a (22.1 0.12 20 air 2 h, then Et3N (0.05 50 %) another h. directly subjected flash column chromatography on silica gel (eluent: petroleum ether/dichloromethane/diethyl ether = 7∶1∶1) afford product 4b. 5a L3-PrEt2Me (4.7 THF 4-phenylpyridine (15.5 3b (18.7 36 (petroleum ether/dichlorometane/ethyl acetate 6:1:1 4∶1) 6a. Results Discussion In initial study, employed 1a electrophile trap intermediate, formed diethyl allenedicarboxylate 3a, optimize (Table 1). preliminary screening, when carried out without ligand/metal salt complex, desired 4a obtained 63% yield diastereoselectivity (2.6∶1 dr), revealing existence 1, entry Next, several salts coordinating N,N′-dioxide L3-PiPr2 tested °C. L3-PiPr2/Mg(OTf)2 promote give 60% yield, >19∶1 diastereomeric ratio (dr), 38% enantiomeric excess (ee) along small amount exocyclic alkene Int-4a (entry 2). When changed into Ni(OTf)2 Zn(OTf)2, but racemic (entries 3 4). surprise, rare-earth used, Y(OTf)3 Yb(OTf)3, nearly optically pure opposite configuration 5 6). Combined previous work40 (see Supporting Information), thought YIII YbIII led deprotection (N-Boc) kinetic resolution process N,N′-dioxide. Subsequent investigation ligands gave better than L3-Pr L3-Ra 7–9). Lowering temperature slightly improved enantioselectivity lower 10). used instead dipolarophile reducing concentration, 4b 73% >19:1 dr 94% ee 12). It should noted accelerate transformation Int-4b higher 13 see Information). reduced reactivity precluded Thus, optimized established 14, 92% dr, ee). Table Optimization Conditions Construction Chiral 1,2-Dihydroisoquinolinesa Entry Metal Salt Ligand T (°C) Yield (%)b drc (%)c — 63 2.6∶1 0 60 38 82 11∶1 4 Zn(OTf)2 54 −99 6 Yb(OTf)3 31 7 81 86 8 77 57 9 64 75 69 18∶1 90 11d 71 91 12d–e 73 94 13d–f 88 14d–g 92 aUnless otherwise noted, all (0.10 mmol), Ligand/metal (1:1, bIsolated yield. cDetermined high-performance liquid (HPLC) supercritical-fluid (SFC) using stationary phase. dPerformed (0.12 mmol). eIn mL). fAt (50 gH2O With hand, substrate scope synthesizing 1,2-dihydroisoquinoline examined Changing ester group iso-propyl steric methyl, ethyl, benzyl, bulkier tert-butyl 2-adamantyl group, diastereoselectivities basically maintained 4a– 4f, 65–92% 10:1–>19:1 85–95% 3-ethylthioester, 3-heteroaromatic ring, 3-benzoyl group-substituted tolerated delivering 4g– 4l (63–80% 71–99% electron-donating substituents (R2) phenyl ring oxindole smoothly converted corresponding cycloaddition 4m– 4q 64–77% 73–99% ee. By comparison, substrates bearing electron-withdrawing yielded π-system 4r– 4t, 54–75% 82–84% variations isoquinolines studied. Generally, different (both -withdrawing C4, C5, C6, C8 positions) reacted form dihydroisoquinoline 4u– 4ad) 52–86% (10:1–>19:1 dr) (78–96% Functional (cyano, nitro) attached precursors amides amines 4w 4ab). investigated effect 4ag isopropyl value 4ag, 86% absolute 4x determined (2′S, 3R, 11b′R) single-crystal X-ray diffraction analysis.a Substrate Scope μL), H/Mg(OTf)2 1H NMR spectroscopy, HPLC SFC bPerformed turned attention nitrogen-containing heterocycles, allenoate.31 Under aforementioned conditions, 4-phenyl 6a results. Upon switching prolonging time h adding base, 77% single diastereomer Information S7). pyridines 3). C4 positions delivered products, exhibited 6b 6c vs 6d). 3-substituted pyridines, diastereo- preserved. However, regioselective situation observed annulation step significantly affected hindrance electronic effect. 3-methyl, 3-chloro, 3-bromo, 3-iodo-substituted took place preferentially hindered C6 position 6e– 6h). Nonetheless, regioselectivity 3-chloride 3-bromo-pyridine 6f/ 6f′ 1.7:1, 6g/ 6g′ 4.8:1). (3-OMe) occurred C2 position, while 6j (3-CN). 3,5-disubstituted lie substituents. 3-bromo-5-fluoropyridine 5k) employed, normal selective 6k 78% 96% ee, 3-bromo-5-methylpyridine 5l). worth noting special selectivity has rarely respect pyridinium salts, pyridine-bearing groups.41–43 1,2-Dihydropyridine Derivativesa L3-PrEt2Me/Mg(OTf)2 (1∶1, (rr) spectroscopy crude product. view utility N-heterocycles, other kinds N-heteroaromatic 3-Methoxy 6-bromoquinolines transformed 8a 8b, enantioselectivitivities obtained, albeit yields. Phthalazine 8c 35% 91% Phenanthridine well, 8d poor (26% 47% Benzimidazole, benzothiazole, benzoxazole did not proceed Investigation Other Heteroaromatic Compoundsa 24 acetanilide internal standard. cPerformed 48 show current system, scale-up 4d performed. shown 2a, 1d (2.5 (3.0 83% 93% Moreover, derivatizations conducted. oxidized m-CPBA generate expected epoxide 9a Treatment Pd/C 60-bar hydrogen pressures, hexahydropyridine derivative 9b 62% 2b). 8′S, 9a′R) N-Ts protected 9b′ Information).b system capable behaving diene Diels–Alder reactions.12,13 example, react dimethyl but-2-ynedioate bridged 9d stereoselectivity 9d, 23% Gram-scale derivatization. get insight mechanism, out. First, deuterium-labelling performed clarify 1,3-H shift process. equiv D2O 75% deuterated [D]- being observed. Furthermore, deuterium-labeled [D2]-3a (88% equivalent amounts [D2]-4a 80.5% D. Even days, completely final products. These two deuterium experiment consistent intramolecular analyzed 3b). obvious Int-6a transferred went (a–c) Control mechanism. Based work,30–32,44–46,c possible pathway 3c). Initially, zwitterion Int-1 situ 2a) diethylallenedicarboxylate 3a). β-Si face H/Mg(II) shielded neighboring cyclohexyl ligand, simultaneous Si/β-Re attack based diastereoselectivities, Int-4b. Nevertheless, step-wise addition/ring closure cannot ruled out.25 Finally, base accelerated [1,3]-hydrogen furnish isomerized Conclusion described dearomatizing zwitterions N,N′-dioxide/Mg(OTf)2 catalyst. (up 99% ee), 1,2-dihydroquinolines, 1,2-dihydropyridines, so on. additives elucidated experiments. cycle explain origin stereoinduction. Footnotes CCDC 2032911 4x) contains supplementary crystallographic data paper. free charge Cambridge Crystallographic Data Centre. b 2051882 9b′) 2023083 [(S)- L3-PicH/Mg(II)] available includes general information, synthesis, experimental procedures, optimization details, experiments, transformations, data, characterization copies SFC, HPLC, CD, spectra. Conflict Interest There no conflict interest report. Funding authors appreciate financial support National Natural Science Foundation China (grant no. 21772127). Acknowledgments wish acknowledge Dr. Yuqiao Zhou (Sichuan University) his assistance analysis. References 1. Fattorusso E., TaglialatelaScafati O., Eds. Modern Alkaloids: Structure, Isolation, Synthesis Biology; Wiley-VCH: Weinheim, Germany, 2008. Google Scholar 2. Vitaku E.; Smith T.; Njardarson J. T.Analysis Structural Diversity, Substitution Patterns, Frequency Nitrogen Heterocycles among FDA Approved Pharmaceuticals.J. Med. Chem.2014, 57, 10257–10274. 3. Taylor R. 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E-Y.; Sun Yao Yan C-G.Synthesis Zwitterionic Salts Three Component Nitrogencontaining Heterocycles, Acetylenedicarboxylate Cyclic 1,3-Dicarbonyl Compounds.Tetrahedron2010, 66, 3569–3574. 45. Esmaeili Zarifi Moradi Izadyar Fakhari R.Diastereoselective Highly Functionalized Quinolizines Pyridine-Based DFT Mechanism.Tetrahedron Lett.2014, 333–337. 46. Ojha Bansal K.Generation Trapping Non-Aromatic Cycloimines Diazotization/Dediazotization N-Amino Amines: Theoretical Results.Struct. Chem.2020, 31, 2179–2187. Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentVolume 4Issue 6Page: 2000-2008Supporting Copyright & Permissions© 2021 Chinese Chemical SocietyKeywordsdihydropyridineasymmetric catalysischiral NN′-dioxidemulticomponent reactionsdearomatizationdihydroisoquinolineAcknowledgmentsThe Downloaded 1,984 times PDF DownloadLoading ...

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