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Lolu cwaningo lubika indlela ephumelela kakhulu yokwenziwa kwama-benzoxazoles kusetshenziswa i-catechol, i-aldehyde kanye ne-ammonium acetate njenge-feedstock ngokusebenzisa ukusabela kokuhlanganisa ku-ethanol ne-ZrCl4 njenge-catalyst. Uchungechunge lwama-benzoxazoles (izinhlobo ezingu-59) lwenziwe ngempumelelo ngale ndlela ngezinzuzo ezifika ku-97%. Ezinye izinzuzo zale ndlela zifaka phakathi ukwenziwa okukhulu kanye nokusetshenziswa komoya-mpilo njenge-oxidizing agent. Izimo zokusabela ezithambile zivumela ukusebenza okulandelayo, okusiza ukwenziwa kwezinto ezahlukahlukene ezihambisana nezakhiwo ezihambisana ne-biology njenge-β-lactams kanye ne-quinoline heterocycles.
Ukuthuthukiswa kwezindlela ezintsha zokwenziwa kwezinto eziphilayo ezinganqoba imikhawulo ekutholeni amakhemikhali anenani eliphezulu futhi kwandiswe ukuhlukahluka kwawo (ukuvula izindawo ezintsha ezingaba khona zokusetshenziswa) kudonsele ukunaka okukhulu kokubili kwezemfundo kanye nasembonini1,2. Ngaphezu kokusebenza kahle kwalezi zindlela, ubungane bemvelo bezindlela ezithuthukiswayo buzoba yinzuzo enkulu3,4.
Ama-Benzoxazole ayisigaba samakhemikhali angenawo umjikelezo adonsele ukunaka okukhulu ngenxa yemisebenzi yawo ecebile yezinto eziphilayo. Lawa makhemikhali kubikwe ukuthi anemisebenzi yokulwa namagciwane, ukuvikela imizwa, ukulwa nomdlavuza, ukulwa namagciwane, ukulwa namagciwane, ukulwa ne-antifungal, kanye nokulwa nokuvuvukala5,6,7,8,9,10,11. Asetshenziswa kabanzi emikhakheni ehlukahlukene yezimboni kufaka phakathi imithi, izinzwa, i-agrochemistry, ama-ligands (ekuguquleni i-metal catalysis), kanye nesayensi yezinto12,13,14,15,16,17. Ngenxa yezakhiwo zawo zamakhemikhali ezihlukile kanye nokuguquguquka kwazo, ama-benzoxazole abe yizinto ezibalulekile zokwakha ukwakheka kwama-molecule amaningi ayinkimbinkimbi e-organic18,19,20. Ngokuthakazelisayo, amanye ama-benzoxazole ayimikhiqizo yemvelo ebalulekile kanye nama-molecule ahlobene nemithi, njenge-nakijinol21, i-boxazomycin A22, i-calcimycin23, i-tafamidis24, i-cabotamycin25 kanye ne-neosalvianene (Isithombe 1A)26.
(A) Izibonelo zemikhiqizo yemvelo esekwe ku-benzoxazole kanye namakhemikhali asebenzayo emzimbeni. (B) Eminye imithombo yemvelo yama-catechol.
Ama-Catechol asetshenziswa kabanzi emikhakheni eminingi efana nemithi, izimonyo kanye nesayensi yezinto zokwakha27,28,29,30,31. Ama-Catechol nawo aboniswe ukuthi anezakhiwo zokulwa ne-antioxidant kanye nokulwa nokuvuvukala, okwenza abe ngabasebenzi abangaba khona njengezinto zokwelapha32,33. Lesi sici siholele ekusetshenzisweni kwawo ekuthuthukisweni kwezimonyo zokulwa nokuguga kanye nemikhiqizo yokunakekelwa kwesikhumba34,35,36. Ngaphezu kwalokho, ama-catechol aboniswe ukuthi angaba yizinto eziphumelelayo zokwenziwa kwezinto eziphilayo (Isithombe 1B)37,38. Amanye ala ma-catechol atholakala kakhulu ngokwemvelo. Ngakho-ke, ukusetshenziswa kwawo njengezinto zokusetshenziswa noma izinto zokuqala zokwenziwa kwezinto eziphilayo kungahlanganisa isimiso se-green chemistry "sokusebenzisa izinsiza ezivuselelekayo". Izindlela eziningana ezahlukene ziye zathuthukiswa ukulungiselela ama-benzoxazole asebenzayo7,39. Ukusebenza kwe-oxidative kwesibopho se-C(aryl)-OH sama-catechol kungenye yezindlela ezithakazelisayo kakhulu nezintsha zokwenziwa kwama-benzoxazoles. Izibonelo zale ndlela ekwakhiweni kwama-benzoxazoles ukusabela kwama-catechol nama-amine40,41,42,43,44, nama-aldehydes45,46,47, nama-alcohols (noma ama-ether)48, kanye nama-ketones, ama-alkenes nama-alkynes (Isithombe 2A)49. Kulolu cwaningo, kusetshenziswe ukusabela okunezingxenye eziningi (i-MCR) phakathi kwe-catechol, i-aldehyde kanye ne-ammonium acetate ekwakhiweni kwama-benzoxazoles (Isithombe 2B). Ukusabela kwenziwa kusetshenziswa inani le-catalytic le-ZrCl4 ku-ethanol solvent. Qaphela ukuthi i-ZrCl4 ingabhekwa njenge-green Lewis acid catalyst, iyi-compound engenabo ubuthi [LD50 (ZrCl4, ngomlomo wamagundane) = 1688 mg kg−1] futhi ayibhekwa njengenobuthi obukhulu50. Ama-catalyst e-Zirconium nawo asetshenziswe ngempumelelo njenge-catalysts ekwakhiweni kwama-compound ahlukahlukene e-organic. Izindleko zazo eziphansi kanye nokuqina okuphezulu emanzini kanye nomoya-mpilo kuzenza zibe yizinto ezikhuthazayo ekuhlanganisweni kwezinto eziphilayo51.
Ukuze sithole izimo zokusabela ezifanele, sikhethe i-3,5-di-tert-butylbenzene-1,2-diol 1a, i-4-methoxybenzaldehyde 2a kanye nosawoti we-ammonium 3 njengezibonelo zokusabela futhi senza ukusabela lapho kukhona ama-Lewis acid ahlukene (LA), izinyibilikisi ezahlukene kanye namazinga okushisa ukuze kwenziwe i-benzoxazole 4a (Ithebula 1). Akukho mkhiqizo owabonwa lapho kungekho khona i-catalyst (Ithebula 1, ukungena 1). Ngemva kwalokho, ama-5 mol % ama-Lewis acid ahlukene njenge-ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 kanye ne-MoO3 ahlolwe njenge-catalysts ku-EtOH solvent kanti i-ZrCl4 yatholakala ingcono kakhulu (Ithebula 1, okufakiwe 2–8). Ukuze kuthuthukiswe ukusebenza kahle, kwahlolwa izinyibilikisi ezahlukene okuhlanganisa i-dioxane, i-acetonitrile, i-ethyl acetate, i-dichloroethane (DCE), i-tetrahydrofuran (THF), i-dimethylformamide (DMF) kanye ne-dimethyl sulfoxide (DMSO). Isivuno sazo zonke izinyibilikisi ezivivinyiwe sasiphansi kunese-ethanol (Ithebula 1, okufakiwe 9-15). Ukusebenzisa eminye imithombo ye-nitrogen (njenge-NH4Cl, i-NH4CN kanye ne-(NH4)2SO4) esikhundleni se-ammonium acetate akuzange kuthuthukise isivuno sokusabela (Ithebula 1, okufakiwe 16-18). Izifundo ezengeziwe zibonise ukuthi amazinga okushisa angaphansi nangaphezu kuka-60 °C awazange akhulise isivuno sokusabela (Ithebula 1, okufakiwe 19 kanye no-20). Lapho umthwalo we-catalyst ushintshwa waba ngu-2 no-10 mol %, isivuno sasingu-78% kanye no-92%, ngokulandelana (Ithebula 1, okufakiwe 21 kanye no-22). Isivuno sehlile lapho ukusabela kwenziwa ngaphansi komkhathi we-nitrogen, okubonisa ukuthi umoya-mpilo womkhathi ungadlala indima ebalulekile ekuphenduleni (Ithebula 1, ukungena 23). Ukwandisa inani le-ammonium acetate akuzange kuthuthukise imiphumela yokusabela futhi kwanciphisa ngisho nokukhiqiza (Ithebula 1, ukungena 24 no-25). Ngaphezu kwalokho, akukho ntuthuko ekuvuneni kokusabela okubonwe ngokwandisa inani le-catechol (Ithebula 1, ukungena 26).
Ngemva kokunquma izimo zokusabela ezifanele, kwafundwa ukuguquguquka nokusebenza kokusabela (Isithombe 3). Njengoba ama-alkynes nama-alkenes enamaqembu abalulekile okusebenza ekuhlanganisweni kwezinto eziphilayo futhi kulula ukuwasebenzisa ukuze aqhubeke nokukhishwa, ama-derivatives amaningana e-benzoxazole ahlanganiswe nama-alkenes nama-alkynes (4b–4d, 4f–4g). Kusetshenziswa i-1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde njenge-substrate ye-aldehyde (4e), isivuno safinyelela ku-90%. Ngaphezu kwalokho, ama-benzoxazoles afakwe esikhundleni se-alkyl halo ahlanganiswe ngezivuno eziphezulu, angasetshenziswa ukuhlanganiswa namanye ama-molecule kanye nokukhishwa okwengeziwe (4h–4i) 52. I-4-((4-fluorobenzyl)oxy)benzaldehyde kanye ne-4-(benzyloxy)benzaldehyde zinikeze ama-benzoxazoles ahambisanayo i-4j kanye ne-4k ngezivuno eziphezulu, ngokulandelana. Sisebenzisa le ndlela, siphumelele ukuhlanganisa ama-benzoxazole derivatives (4l kanye no-4m) aqukethe ama-quinolone moieties53,54,55. I-Benzoxazole 4n equkethe amaqembu amabili e-alkyne yakhiqizwa ngo-84% wesivuno esivela kuma-benzaldehydes angu-2,4 athathelwe indawo. I-Bicyclic compound 4o equkethe i-indole heterocycle yakhiqizwa ngempumelelo ngaphansi kwezimo ezilungiselelwe kahle. I-Compound 4p yakhiqizwa kusetshenziswa i-aldehyde substrate enamathiselwe eqenjini le-benzonitrile, okuyi-substrate ewusizo yokulungiselela ama-supramolecule e-(4q-4r)56. Ukuze kugqanyiswe ukusebenza kwale ndlela, ukulungiswa kwama-molecule e-benzoxazole aqukethe ama-β-lactam moieties (4q-4r) kwaboniswa ngaphansi kwezimo ezilungiselelwe kahle ngokusebenzisa ukusabela kwama-β-lactam asebenzayo e-aldehyde, i-catechol, kanye ne-ammonium acetate. Lokhu kuhlola kubonisa ukuthi indlela entsha yokwenziwa ingasetshenziswa ekusebenzeni kwesigaba sokugcina kwama-molecule ayinkimbinkimbi.
Ukuze siqhubeke nokukhombisa ukuguquguquka nokubekezelelana kwale ndlela kumaqembu asebenzayo, sifunde ama-aldehyde ahlukahlukene anuka kamnandi okuhlanganisa amaqembu anikela ngama-electron, amaqembu akhipha ama-electron, ama-heterocyclic compounds, kanye nama-polycyclic aromatic hydrocarbons (Isithombe 4, 4s–4aag). Isibonelo, i-benzaldehyde yaguqulwa yaba umkhiqizo ofiselekayo (4s) ngesivuno esingu-92% esihlukanisiwe. Ama-aldehyde anuka kamnandi anamaqembu anikela ngama-electron (kufaka phakathi i--Me, i-isopropyl, i-tert-butyl, i-hydroxyl, kanye ne-para-SMe) aguqulwa ngempumelelo abe yimikhiqizo ehambisanayo ngesivuno esihle kakhulu (4t–4x). Ama-substrates e-aldehyde avinjelwe yi-sterically angakhiqiza imikhiqizo ye-benzoxazole (4y–4aa, 4al) ngesivuno esihle kuya kwesihle kakhulu. Ukusetshenziswa kwama-benzaldehydes ashintshiwe nge-meta (4ab, 4ai, 4am) kwavumela ukulungiswa kwemikhiqizo ye-benzoxazole ngesivuno esiphezulu. Ama-aldehyde e-halogenated afana ne-(-F, -CF3, -Cl kanye ne-Br) anikeze ama-benzoxazoles ahambisanayo (4af, 4ag kanye ne-4ai-4an) ngesivuno esanelisayo. Ama-Aldehydes anamaqembu okuhoxisa ama-electron (isb. -CN kanye ne-NO2) nawo asabela kahle futhi anikeza imikhiqizo efiselekayo (4ah kanye ne-4ao) ngesivuno esiphezulu.
Uchungechunge lokusabela olusetshenziselwa ukwenziwa kwama-aldehydes a kanye no-b. a Izimo zokusabela: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) kanye no-ZrCl4 (5 mol%) kwasabela ku-EtOH (3 mL) ku-60 °C amahora ayi-6. b Isivuno sihambisana nomkhiqizo ohlukanisiwe.
Ama-aldehyde e-polycyclic aromatic afana ne-1-naphthaldehyde, i-anthracene-9-carboxaldehyde kanye ne-phenanthrene-9-carboxaldehyde angakhiqiza imikhiqizo efiselekayo engu-4ap-4ar ngezivuno eziphezulu. Ama-aldehyde ahlukahlukene e-heterocyclic aromatic alloyment afaka phakathi i-pyrrole, i-indole, i-pyridine, i-furan kanye ne-thiophene abekezelela kahle izimo zokusabela futhi angakhiqiza imikhiqizo ehambisanayo (4as-4az) ngezivuno eziphezulu. I-Benzoxazole 4aag itholakale ngezivuno ezingu-52% kusetshenziswa i-aldehyde ehambisanayo ye-aliphatic.
Indawo yokusabela kusetshenziswa ama-aldehyde okuhweba a, b. a Izimo zokusabela: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) kanye ne-ZrCl4 (5 mol %) zasabela ku-EtOH (5 mL) ku-60 °C amahora ama-4. b Isivuno sihambisana nomkhiqizo ohlukanisiwe. c Ukusabela kwenziwa ku-80 °C amahora ama-6; d Ukusabela kwenziwa ku-100 °C amahora angama-24.
Ukuze sibonise kabanzi ukusebenza ngendlela ehlukahlukene kanye nokusebenza kwale ndlela, siphinde sahlola ama-catechol ahlukahlukene afakwe esikhundleni. Ama-catechol afakwe esikhundleni esisodwa njenge-4-tert-butylbenzene-1,2-diol kanye ne-3-methoxybenzene-1,2-diol asabela kahle ngale nqubo, okwenza ama-benzoxazoles angu-4aaa–4aac abe yi-89%, 86%, kanye ne-57% yenzuzo, ngokulandelana. Amanye ama-benzoxazoles afakwe esikhundleni se-poly aphinde akhiqizwa ngempumelelo kusetshenziswa ama-catechol afakwe esikhundleni se-poly (4aad–4aaf). Akukho mikhiqizo etholakale lapho kusetshenziswa ama-catechol afakwe esikhundleni se-electron angenawo ama-electron njenge-4-nitrobenzene-1,2-diol kanye ne-3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
Ukwenziwa kwe-benzoxazole ngamanani amagremu kwenziwe ngempumelelo ngaphansi kwezimo ezilungiselelwe kahle, kanti i-compound 4f yakhiqizwa ngesivuno esingu-85% esihlukanisiwe (Isithombe 5).
Ukwenziwa kwe-benzoxazole 4f ngesilinganiso se-gram. Izimo zokusabela: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) kanye ne-ZrCl4 (5 mol%) kwasabela ku-EtOH (25 mL) ku-60 °C amahora ama-4.
Ngokusekelwe kudatha yezincwadi, kuye kwaphakanyiswa indlela yokusabela efanelekile yokwenziwa kwama-benzoxazoles avela ku-catechol, aldehyde, kanye ne-ammonium acetate lapho kukhona i-catalyst ye-ZrCl4 (Isithombe 6). I-Catechol ingakhipha i-zirconium ngokuxhumanisa amaqembu amabili e-hydroxyl ukwakha umongo wokuqala womjikelezo we-catalytic (I)51. Kulesi simo, i-semiquinone moiety (II) ingakhiwa nge-enol-keto tautomerization ku-complex I58. Iqembu le-carbonyl elakhiwe ku-intermediate (II) ngokusobala lisabela ne-ammonium acetate ukwakha i-intermediate imine (III) 47. Okunye okungenzeka ukuthi i-imine (III^), eyakhiwa ukusabela kwe-aldehyde ne-ammonium acetate, isabela neqembu le-carbonyl ukwakha i-intermediate imine-phenol (IV) 59,60. Ngemva kwalokho, i-intermediate (V) ingadlula i-intramolecular cyclization40. Ekugcineni, i-intermediate V ixutshwa nomoya-mpilo womoya, ikhiphe umkhiqizo ofiselekayo 4 bese ikhulula i-zirconium complex ukuze kuqalwe umjikelezo olandelayo 61,62.
Zonke izinto zokwenziwa kanye nezinyibilikisi zathengwa emithonjeni yezentengiselwano. Yonke imikhiqizo eyaziwayo yatholakala ngokuqhathaniswa nedatha ye-spectral kanye namaphuzu okuncibilika kwamasampula ahlolwe. Ama-spectra angu-1H NMR (400 MHz) kanye ne-13C NMR (100 MHz) aqoshwe kuthuluzi le-Brucker Avance DRX. Amaphuzu okuncibilika atholwe kuthuluzi le-Büchi B-545 ku-capillary evulekile. Zonke izimpendulo zaqashwa yi-chromatography enongqimba oluncane (TLC) kusetshenziswa amapuleti e-silica gel (i-Silica gel 60 F254, i-Merck Chemical Company). Ukuhlaziywa kwe-elemental kwenziwa ku-PerkinElmer 240-B Microanalyzer.
Isixazululo se-catechol (1.0 mmol), i-aldehyde (1.0 mmol), i-ammonium acetate (1.0 mmol) kanye ne-ZrCl4 (5 mol %) ku-ethanol (3.0 mL) savuselelwa ngokulandelana epayipini elivulekile ebhavini lamafutha ku-60 °C ngaphansi komoya isikhathi esidingekayo. Intuthuko yokusabela yaqashwa nge-thin layer chromatography (TLC). Ngemva kokuphothulwa kokusabela, ingxube ephumayo yapholiswa ekushiseni kwegumbi futhi i-ethanol yasuswa ngaphansi kwengcindezi encishisiwe. Ingxube yokusabela yaxutshwa ne-EtOAc (3 x 5 mL). Ngemuva kwalokho, izendlalelo eziphilayo ezihlanganisiwe zomiswa phezu kwe-Na2SO4 engenamanzi futhi zagxishwa ku-vacuo. Ekugcineni, ingxube eluhlaza yahlanzwa nge-column chromatography kusetshenziswa i-petroleum ether/EtOAc njenge-eluent ukuze kutholakale i-benzoxazole 4 emsulwa.
Ngamafuphi, sithuthukise inqubo entsha, emnene neluhlaza yokwenziwa kwama-benzoxazoles ngokwakhiwa okulandelanayo kwama-CN kanye nama-CO bonds lapho kukhona i-zirconium catalyst. Ngaphansi kwezimo zokusabela ezilungiselelwe, ama-benzoxazoles ahlukene angu-59 akhiwe. Izimo zokusabela ziyahambisana namaqembu ahlukahlukene asebenzayo, futhi ama-core amaningana asebenzayo akhiwe ngempumelelo, okubonisa amandla awo aphezulu okusebenza okulandelayo. Ngakho-ke, sithuthukise isu elisebenzayo, elilula nelisebenzayo lokukhiqizwa okukhulu kwezinhlobo ezahlukene ze-benzoxazole ezivela kuma-catechol emvelo ngaphansi kwezimo eziluhlaza kusetshenziswa ama-catalysts ashibhile.
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