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Phuputso ena e tlaleha mokhoa o sebetsang hantle haholo oa ho kopanya li-benzoxazole ho sebelisoa catechol, aldehyde le ammonium acetate e le lijo ka karabelo ea ho kopanya ethanol le ZrCl4 e le catalyst. Letoto la li-benzoxazole (mefuta e 59) li ile tsa hlahisoa ka katleho ke mokhoa ona ka chai e fihlang ho 97%. Melemo e meng ea mokhoa ona e kenyelletsa ho kopanya ka bongata le tšebeliso ea oksijene e le moemeli oa oxidizing. Maemo a karabelo a bonolo a lumella ts'ebetso e latelang, e nolofalletsang ho kopanya li-derivatives tse fapaneng tse nang le meaho e amanang le baeloji joalo ka β-lactams le quinoline heterocycles.
Ntlafatso ea mekhoa e mecha ea tlhahiso ea lintho tse phelang e ka hlōlang lithibelo tsa ho fumana metsoako ea boleng bo holimo le ho eketsa mefuta-futa ea eona (ho bula libaka tse ncha tse ka sebelisoang) e hohetse tlhokomelo e kholo thutong le indastering1,2. Ntle le bokhoni bo phahameng ba mekhoa ena, botsoalle ba tikoloho ba mekhoa e ntseng e ntlafatsoa le eona e tla ba molemo o moholo3,4.
Benzoxazoles ke sehlopha sa metsoako e sa fetoheng e hohetseng tlhokomelo e kholo ka lebaka la mesebetsi ea eona e ruileng ea baeloji. Metsoako e joalo e tlalehiloe e na le mesebetsi ea ho loantša likokoana-hloko, ho sireletsa methapo ea kutlo, ho loantša kankere, ho loantša kokoana-hloko, ho loantša likokoana-hloko, ho loantša likokoana-hloko, le ho thibela ho ruruha5,6,7,8,9,10,11. Li boetse li sebelisoa haholo masimong a fapaneng a indasteri ho kenyeletsoa meriana, li-sensorics, agrochemistry, ligands (bakeng sa phetoho ea tšepe ea catalysis), le saense ea thepa12,13,14,15,16,17. Ka lebaka la litšobotsi tsa tsona tse ikhethang tsa lik'hemik'hale le ho tenyetseha ha tsona, benzoxazoles e fetohile litene tsa bohlokoa bakeng sa ho kopanya limolek'hule tse ngata tse rarahaneng tsa tlhaho18,19,20. Hoa thahasellisa hore li-benzoxazoles tse ling ke lihlahisoa tsa bohlokoa tsa tlhaho le limolek'hule tse amanang le meriana, tse kang nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 le neosalvianene (Setšoantšo sa 1A)26.
(A) Mehlala ea lihlahisoa tsa tlhaho tse thehiloeng ho benzoxazole le metsoako e sebetsang ea baeloji. (B) Mehloli e meng ea tlhaho ea likatekesi.
Li-catechol li sebelisoa haholo masimong a mangata a kang meriana, litlolo le saense ea thepa27,28,29,30,31. Li-catechol le tsona li bontšitsoe li na le thepa ea antioxidant le anti-inflammatory, e leng se etsang hore e be bakhethoa ba ka bang li-agent tsa kalafo32,33. Thepa ena e lebisitse tšebelisong ea eona nts'etsopele ea litlolo tse thibelang botsofali le lihlahisoa tsa tlhokomelo ea letlalo34,35,36. Ho feta moo, li-catechol li bontšitsoe e le li-precursor tse sebetsang bakeng sa tlhahiso ea lintho tse phelang (Setšoantšo sa 1B)37,38. Tse ling tsa li-catechol tsena li ngata haholo ka tlhaho. Ka hona, tšebeliso ea eona e le thepa e tala kapa thepa ea ho qala tlhahiso ea lintho tse phelang e ka kenyelletsa molao-motheo oa k'hemistri e tala oa "ho sebelisa mehloli e nchafatsoang". Litsela tse 'maloa tse fapaneng li ntlafalitsoe ho lokisa metsoako ea benzoxazole e sebetsang7,39. Ts'ebetso ea oxidative ea tlamo ea C(aryl)-OH ea li-catechol ke e 'ngoe ea mekhoa e khahlisang le e ncha ea ho kopanya li-benzoxazoles. Mehlala ea mokhoa ona oa ho kopanya benzoxazoles ke liketso tsa catechol le amines40,41,42,43,44, le aldehydes45,46,47, le alcohols (kapa ethers)48, hammoho le li-ketones, alkenes le alkynes (Setšoantšo sa 2A)49. Thutong ena, karabelo ea likarolo tse ngata (MCR) pakeng tsa catechol, aldehyde le ammonium acetate e sebelisitsoe bakeng sa ho kopanya benzoxazoles (Setšoantšo sa 2B). Karabelo e entsoe ho sebelisoa bongata ba catalytic ba ZrCl4 ka har'a ethanol solvent. Hlokomela hore ZrCl4 e ka nkoa e le catalyst e tala ea Lewis acid, ke motsoako o se nang chefo e ngata [LD50 (ZrCl4, o nooang bakeng sa likhoto) = 1688 mg kg−1] 'me ha e nkoe e le chefo e ngata50. Li-catalyst tsa Zirconium le tsona li sebelisitsoe ka katleho e le li-catalyst bakeng sa ho kopanya metsoako e fapaneng ea lintho tse phelang. Litšenyehelo tsa tsona tse tlase le botsitso bo phahameng ba metsi le oksijene li etsa hore e be li-catalyst tse tšepisang tlhahisong ea lintho tse phelang51.
Ho fumana maemo a loketseng a karabelo, re khethile 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a le letsoai la ammonium 3 e le likarabelo tsa mohlala mme ra etsa likarabelo moo ho nang le li-asidi tse fapaneng tsa Lewis (LA), li-solvent tse fapaneng le mocheso ho etsa benzoxazole 4a (Tafole ea 1). Ha ho sehlahisoa se ileng sa bonoa ha ho se na catalyst (Tafole ea 1, ho kena ha 1). Ka mor'a moo, 5 mol % ea li-asidi tse fapaneng tsa Lewis tse kang ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 le MoO3 li ile tsa lekoa e le li-catalyst ho EtOH solvent 'me ZrCl4 e fumanoe e le eona e ntle ka ho fetisisa (Tafole ea 1, li-entries tsa 2–8). Ho ntlafatsa bokgoni, ho ile ha lekoa ditharollo tse fapaneng ho kenyeletsoa dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) le dimethyl sulfoxide (DMSO). Dihlahiswa tsa ditharollo tsohle tse lekilweng di ne di le tlase ho feta tsa ethanol (Tafole ya 1, dikenyo 9-15). Ho sebedisa mehlodi e meng ya naetrojene (jwalo ka NH4Cl, NH4CN le (NH4)2SO4) sebakeng sa ammonium acetate ha ho a ka ha ntlafatsa tlhahiso ya karabelo (Tafole ya 1, dikenyo 16-18). Diphuputso tse ding di bontshitse hore dithempereichara tse ka tlase le tse ka hodimo ho 60 °C ha di a ka tsa eketsa tlhahiso ya karabelo (Tafole ya 1, dikenyo 19 le 20). Ha ho kenngwa ha catalyst ho fetoloa ho 2 le 10 mol %, dihlahiswa e ne e le 78% le 92%, ka ho latellana (Tafole ya 1, dikenyo 21 le 22). Kotulo e ile ea fokotseha ha karabelo e etsoa tlas'a sepakapaka sa naetrojene, e leng se bontšang hore oksijene ea sepakapaka e ka bapala karolo ea bohlokoa karabelong (Tafole ea 1, keno ea 23). Ho eketsa bongata ba ammonium acetate ha hoa ka ha ntlafatsa liphetho tsa karabelo 'me ho bile ho fokotsa kotulo (Tafole ea 1, keno ea 24 le 25). Ho phaella moo, ha ho ntlafatso kotulong ea karabelo e ileng ea bonoa ka ho eketsa bongata ba catechol (Tafole ea 1, keno ea 26).
Kamora ho fumana maemo a karabelo a nepahetseng ka ho fetisisa, ho ile ha ithutoa ho tenyetseha le ho sebetsa ha karabelo (Setšoantšo sa 3). Kaha li-alkynes le li-alkenes li na le lihlopha tsa bohlokoa tse sebetsang ho tsoakong ea lintho tse phelang 'me li bonolo ho li fumana, li-derivatives tse' maloa tsa benzoxazole li ile tsa etsoa ka li-alkenes le li-alkynes (4b–4d, 4f–4g). Ho sebelisoa 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde e le substrate ea aldehyde (4e), chai e fihlile ho 90%. Ho phaella moo, li-benzoxazoles tse nkeloang sebaka ke alkyl halo li ile tsa etsoa ka chai e phahameng, e ka sebelisoang bakeng sa ho hokahana le limolek'hule tse ling le ho tsoa ho eona hape (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde le 4-(benzyloxy)benzaldehyde li fane ka benzoxazoles tse tsamaellanang 4j le 4k ka chai e phahameng, ka ho latellana. Re sebelisa mokhoa ona, re atlehile ho kopanya li-derivative tsa benzoxazole (4l le 4m) tse nang le li-moieties tsa quinolone53,54,55. Benzoxazole 4n e nang le lihlopha tse peli tsa alkyne e entsoe ka tlhahiso ea 84% ho tsoa ho benzaldehydes tse 2,4 tse nkeloang sebaka. Bicyclic compound 4o e nang le heterocycle ea indole e entsoe ka katleho tlas'a maemo a ntlafalitsoeng. Compound 4p e entsoe ka ho sebelisa substrate ea aldehyde e hoketsoeng sehlopheng sa benzonitrile, e leng substrate e thusang bakeng sa ho lokisa li-supramolecule tsa (4q-4r)56. Ho totobatsa ts'ebeliso ea mokhoa ona, ho lokisa limolek'hule tsa benzoxazole tse nang le li-moieties tsa β-lactam (4q-4r) ho bontšitsoe tlas'a maemo a ntlafalitsoeng ka karabelo ea li-β-lactam tse sebetsang ka aldehyde, catechol, le ammonium acetate. Liteko tsena li bontša hore mokhoa o sa tsoa ntlafatsoa oa maiketsetso o ka sebelisoa bakeng sa ts'ebetso ea morao-rao ea limolek'hule tse rarahaneng.
Ho bontša ho tenyetseha le mamello ea mokhoa ona ho lihlopha tse sebetsang, re ithutile li-aldehyde tse fapaneng tse nkhang hamonate ho kenyeletsoa lihlopha tse fanang ka li-electron, lihlopha tse hulang li-electron, metsoako ea heterocyclic, le li-hydrocarbon tse nkhang hamonate tsa polycyclic (Setšoantšo sa 4, 4s–4aag). Mohlala, benzaldehyde e fetotsoe ho sehlahisoa se lakatsehang (4s) ka chai e arohaneng ea 92%. Li-aldehyde tse nkhang hamonate tse nang le lihlopha tse fanang ka li-electron (ho kenyeletsoa -Me, isopropyl, tert-butyl, hydroxyl, le para-SMe) li ile tsa fetoloa ka katleho ho ba lihlahisoa tse tsamaellanang ka chai e ntle (4t–4x). Li-substrate tsa aldehyde tse sitisoang ke sterili li ka hlahisa lihlahisoa tsa benzoxazole (4y–4aa, 4al) ka chai e ntle ho isa ho e ntle. Tšebeliso ea li-benzaldehyde tse nkeloang sebaka ke meta (4ab, 4ai, 4am) e lumelletse ho lokisoa ha lihlahisoa tsa benzoxazole ka chai e phahameng. Li-aldehyde tse nang le halogenated tse kang (-F, -CF3, -Cl le Br) li fane ka benzoxazoles tse tsamaellanang (4af, 4ag le 4ai-4an) ka chai e khotsofatsang. Li-aldehydes tse nang le lihlopha tse hulang li-electron (mohlala, -CN le NO2) le tsona li arabetse hantle 'me li fane ka lihlahisoa tse lakatsehang (4ah le 4ao) ka chai e phahameng.
Letoto la karabelo le sebedisitsweng bakeng sa ho kopanya di-aldehydes a le b. a Maemo a karabelo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) le ZrCl4 (5 mol%) di ile tsa arajwa ho EtOH (3 mL) ho 60 °C ka dihora tse 6. b Poelo e tsamaellana le sehlahiswa se arohaneng.
Li-aldehyde tse nkhang hamonate tse nang le polycyclic tse kang 1-naphthaldehyde, anthracene-9-carboxaldehyde le phenanthrene-9-carboxaldehyde li ka hlahisa lihlahisoa tse lakatsehang tsa 4ap-4ar ka chai e phahameng. Li-aldehyde tse fapaneng tsa heterocyclic aromatic tse kenyeletsang pyrrole, indole, pyridine, furan le thiophene li mamelletse maemo a karabelo hantle 'me li ka hlahisa lihlahisoa tse tsamaellanang (4as-4az) ka chai e phahameng. Benzoxazole 4aag e fumanoe ka chai ea 52% ho sebelisoa aliphatic aldehyde e tsamaellanang.
Sebaka sa karabelo se sebelisang aldehydes tsa khoebo a, b. a Maemo a karabelo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) le ZrCl4 (5 mol %) li ile tsa arajoa ho EtOH (5 mL) ho 60 °C ka lihora tse 4. b Poelo e tsamaellana le sehlahisoa se arohaneng. c Karabelo e entsoe ho 80 °C ka lihora tse 6; d Karabelo e entsoe ho 100 °C ka lihora tse 24.
Ho bontša haholoanyane ho tenyetseha le ho sebetsa ha mokhoa ona, re boetse ra leka li-catechol tse fapaneng tse nketsoeng sebaka. Li-catechol tse nketsoeng sebaka tse kang 4-tert-butylbenzene-1,2-diol le 3-methoxybenzene-1,2-diol li arabetse hantle ka mokhoa ona, li fana ka benzoxazoles 4aaa–4aac ka chai ea 89%, 86%, le 57%, ka ho latellana. Li-benzoxazoles tse ling tse nketsoeng sebaka tse ngata le tsona li entsoe ka katleho ho sebelisoa li-catechol tse nketsoeng sebaka tse tšoanang (4aad–4aaf). Ha ho lihlahisoa tse fumanoeng ha ho sebelisoa li-catechol tse nketsoeng sebaka tse haelloang ke li-electron tse kang 4-nitrobenzene-1,2-diol le 3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
Ho kopanngoa ha benzoxazole ka bongata ba digrama ho ile ha finyelloa ka katleho tlasa maemo a ntlafaditsweng, mme motsoako wa 4f o ile wa kopanngwa ka chai e arohaneng ya 85% (Setshwantsho sa 5).
Ho kopanngoa ha benzoxazole 4f ka tekanyo ea gram. Maemo a karabelo: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) le ZrCl4 (5 mol%) li ile tsa arajoa ho EtOH (25 mL) ho 60 °C ka lihora tse 4.
Ho latela lintlha tsa lingoliloeng, mokhoa o utloahalang oa karabelo o sisintswe bakeng sa ho kopanya benzoxazoles ho tsoa ho catechol, aldehyde, le ammonium acetate moo ho nang le catalyst ea ZrCl4 (Setšoantšo sa 6). Catechol e ka chelate zirconium ka ho hokahanya lihlopha tse peli tsa hydroxyl ho theha motheo oa pele oa potoloho ea catalytic (I)51. Tabeng ena, semiquinone moiety (II) e ka thehoa ka enol-keto tautomerization ho complex I58. Sehlopha sa carbonyl se thehiloeng bohareng (II) ho bonahala se arabela le ammonium acetate ho theha imine e bohareng (III) 47. Monyetla o mong ke hore imine (III^), e entsoeng ke karabelo ea aldehyde le ammonium acetate, e arabela le sehlopha sa carbonyl ho theha imine-phenol e bohareng (IV) 59,60. Ka mor'a moo, medium (V) e ka feta intramolecular cyclization40. Qetellong, V e mahareng e oxidiswa ka oksijene ya sepakapaka, e hlahisa sehlahiswa se lakatsehang sa 4 mme e lokolla motsoako wa zirconium ho qala potoloho e latelang ya 61,62.
Li-reagent tsohle le li-solvent li rekiloe mehloling ea khoebo. Lihlahisoa tsohle tse tsejoang li ile tsa khetholloa ka ho bapisoa le data ea spectral le lintlha tsa ho qhibiliha tsa lisampole tse lekiloeng. Li-spectra tsa 1H NMR (400 MHz) le 13C NMR (100 MHz) li ile tsa tlalehoa sesebelisoa sa Brucker Avance DRX. Lintlha tsa ho qhibiliha li ile tsa fumanoa sesebelisoa sa Büchi B-545 ka har'a capillary e bulehileng. Likarabelo tsohle li ile tsa hlahlojoa ka chromatography e nang le lera le lesesaane (TLC) ho sebelisoa lipoleiti tsa silica gel (Silica gel 60 F254, Merck Chemical Company). Tlhahlobo ea elemental e entsoe ho PerkinElmer 240-B Microanalyzer.
Tharollo ea catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) le ZrCl4 (5 mol %) ka har'a ethanol (3.0 mL) e ile ea hlohlelletsoa ka tatellano ka har'a tube e bulehileng ka bateng ea oli mochesong oa 60 °C tlas'a moea ka nako e hlokahalang. Tsoelo-pele ea karabelo e ile ea hlahlojoa ke thin layer chromatography (TLC). Kamora ho qeta karabelo, motsoako o hlahisitsoeng o ile oa pholisoa mochesong oa kamore 'me ethanol ea tlosoa tlas'a khatello e fokotsehileng. Motsoako oa karabelo o ile oa hlapolloa ka EtOAc (3 x 5 mL). Ebe, likarolo tse kopaneng tsa tlhaho li ile tsa omisoa holim'a Na2SO4 e sa hloekang 'me tsa kenngoa ka vacuo. Qetellong, motsoako o tala o ile oa hloekisoa ka column chromatography ho sebelisoa petroleum ether/EtOAc e le eluent ho fana ka benzoxazole e hloekileng 4.
Ka bokhutšoanyane, re qapile mokhoa o mocha, o bobebe le o motala bakeng sa ho kopanya li-benzoxazole ka ho theha ka tatellano ea libofo tsa CN le CO ka pel'a catalyst ea zirconium. Tlas'a maemo a karabelo a ntlafalitsoeng, li-benzoxazole tse 59 tse fapaneng li ile tsa etsoa. ​​Maemo a karabelo a lumellana le lihlopha tse fapaneng tsa ts'ebetso, 'me li-cores tse' maloa tse sebetsang li ile tsa etsoa ka katleho, e leng se bontšang bokhoni ba tsona bo phahameng ba ts'ebetso e latelang. Ka hona, re qapile leano le sebetsang hantle, le bonolo le le sebetsang bakeng sa tlhahiso e kholo ea li-derivatives tse fapaneng tsa benzoxazole ho tsoa ho li-catechol tsa tlhaho tlas'a maemo a matala re sebelisa li-catalyst tse theko e tlase.
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