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Olu phononongo luxela indlela esebenza kakuhle kakhulu yokwenza i-benzoxazoles kusetyenziswa i-catechol, i-aldehyde kunye ne-ammonium acetate njenge-feedstock ngokusebenzisa i-coupling reaction kwi-ethanol kunye ne-ZrCl4 njenge-catalyst. Uthotho lwe-benzoxazoles (iintlobo ezingama-59) zenziwe ngempumelelo ngale ndlela kwimveliso ukuya kuthi ga kwi-97%. Ezinye iingenelo zale ndlela ziquka ukwenziwa okukhulu kunye nokusetyenziswa kwe-oxygen njenge-oxidizing agent. Iimeko zokusabela ezithambileyo zivumela ukusebenza okulandelayo, okunceda ukwenziwa kwezinto ezahlukeneyo eziphuma kwi-biologically ezifana ne-β-lactams kunye ne-quinoline heterocycles.
Uphuhliso lweendlela ezintsha zokwenziwa kwezinto eziphilayo ezinokoyisa imida ekufumaneni iikhompawundi ezinexabiso eliphezulu kwaye zonyuse ulwahlulo lwazo (ukuvula iindawo ezintsha ezinokubakho zokusetyenziswa) lutsale ingqalelo enkulu kwizifundo nakwishishini1,2. Ukongeza ekusebenzeni kakuhle kwezi ndlela, ukuba nobuhlobo nokusingqongileyo kweendlela eziphuhliswayo kuya kuba yinzuzo ebalulekileyo3,4.
IiBenzoxazoles ziluhlobo lweekhompawundi ze-heterocyclic eziye zatsala ingqalelo enkulu ngenxa yemisebenzi yazo etyebileyo yebhayoloji. Ezi khompawundi ziye zaxelwa ukuba zinemisebenzi yokulwa neentsholongwane, ukuzikhusela kwimithambo-luvo, umhlaza, i-antiviral, i-antibacterial, i-fungal, kunye ne-anti-inflammatory5,6,7,8,9,10,11. Zikwasetyenziswa kakhulu kwiindawo ezahlukeneyo zoshishino kubandakanya amayeza, ii-sensorics, i-agrochemistry, ii-ligands (zokuguqula i-metal catalysis), kunye nesayensi yezinto12,13,14,15,16,17. Ngenxa yeempawu zazo ezikhethekileyo zeekhemikhali kunye nokuguquguquka kwazo, ii-benzoxazoles ziye zaba zizinto ezibalulekileyo zokwakha ukwenziwa kweemolekyuli ezininzi ze-organic ezintsonkothileyo18,19,20. Okunomdla kukuba, ezinye ii-benzoxazoles ziimveliso zendalo ezibalulekileyo kunye neemolekyuli ezifanelekileyo kwi-pharmacological, ezifana ne-nakijinol21, i-boxazomycin A22, i-calcimycin23, i-tafamidis24, i-cabotamycin25 kunye ne-neosalvianene (Umfanekiso 1A)26.
(A) Imizekelo yeemveliso zendalo ezisekelwe kwi-benzoxazole kunye neekhompawundi ezisebenzayo kwindalo. (B) Eminye imithombo yendalo yee-catechol.
IiCatechol zisetyenziswa kakhulu kwiindawo ezininzi ezifana namayeza, izinto zokuthambisa kunye nesayensi yezinto27,28,29,30,31. IiCatechol zikwabonakalisiwe ukuba zineempawu ze-antioxidant kunye ne-anti-inflammatory, nto leyo eyenza ukuba zibe ngabasebenzi abanokuba ngamayeza onyango32,33. Le propati ikhokelele ekusetyenzisweni kwayo ekuphuhlisweni kwezinto zokuthambisa ezilwa nokwaluphala kunye neemveliso zokhathalelo lolusu34,35,36. Ngaphezu koko, iiCatechol zibonakalisiwe njengeziphambili ezisebenzayo zokwenziwa kwezinto eziphilayo (Umfanekiso 1B)37,38. Ezinye zezi catechols zininzi kakhulu kwindalo. Ke ngoko, ukusetyenziswa kwayo njengezinto eziluhlaza okanye izinto zokuqala zokwenziwa kwezinto eziphilayo kunokubandakanya umgaqo wekhemistri eluhlaza "wokusebenzisa izixhobo ezivuselelekayo". Iindlela ezahlukeneyo ziye zaphuhliswa ukulungiselela iikhompawundi ze-benzoxazole ezisebenzayo7,39. Ukusebenza kwe-oxidative kwebhondi ye-C(aryl)-OH yee-catechols yenye yezona ndlela zinomdla nezintsha zokwenziwa kwee-benzoxazoles. Imizekelo yale ndlela yokwenza i-benzoxazoles ziimpendulo ze-catechols kunye ne-amines40,41,42,43,44, kunye ne-aldehydes45,46,47, kunye ne-alcohols (okanye i-ethers)48, kunye ne-ketones, i-alkenes kunye ne-alkynes (Umfanekiso 2A)49. Kolu phononongo, i-multicomponent reaction (MCR) phakathi kwe-catechol, i-aldehyde kunye ne-ammonium acetate yasetyenziswa ekwenzeni i-benzoxazoles (Umfanekiso 2B). I-reaction yenziwe kusetyenziswa isixa se-catalytic se-ZrCl4 kwi-ethanol solvent. Qaphela ukuba i-ZrCl4 ingathathwa njenge-green Lewis acid catalyst, yi-compound engenabungozi [LD50 (ZrCl4, yomlomo kwiimpuku) = 1688 mg kg−1] kwaye ayithathwa njengenobungozi obukhulu50. Ii-catalysts ze-Zirconium nazo zisetyenziswe ngempumelelo njengee-catalysts zokwenziwa kwee-organic compounds ezahlukeneyo. Ixabiso lazo eliphantsi kunye nokuzinza okuphezulu emanzini nakwioksijini kuzenza zibe zii-catalysts ezithembisayo kwi-organic synthesis51.
Ukuze sifumane iimeko ezifanelekileyo zokusabela, sikhethe i-3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a kunye netyuwa ye-ammonium 3 njengeempendulo zemodeli kwaye senze iimpendulo phambi kwee-asidi ezahlukeneyo zeLewis (LA), izinyibilikisi ezahlukeneyo kunye namaqondo obushushu ukwenza i-benzoxazole 4a (Itheyibhile 1). Akukho mveliso ibonwe ngaphandle kwe-catalyst (Itheyibhile 1, ukungena 1). Emva koko, i-5 mol % yee-asidi ezahlukeneyo zeLewis ezifana ne-ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 kunye ne-MoO3 zavavanywa njengee-catalysts kwi-solvent ye-EtOH kwaye i-ZrCl4 yafunyanwa iyeyona ilungileyo (Itheyibhile 1, ukungena 2–8). Ukuphucula ukusebenza kakuhle, kuye kwavavanywa izinyibilikisi ezahlukeneyo kuquka i-dioxane, i-acetonitrile, i-ethyl acetate, i-dichloroethane (DCE), i-tetrahydrofuran (THF), i-dimethylformamide (DMF) kunye ne-dimethyl sulfoxide (DMSO). Imveliso yazo zonke izinyibilikisi ezivavanyiweyo ibiphantsi kuneye-ethanol (Itheyibhile 1, iingeniso 9–15). Ukusebenzisa eminye imithombo ye-nitrogen (efana ne-NH4Cl, i-NH4CN kunye ne-(NH4)2SO4) endaweni ye-ammonium acetate akuzange kuyiphucule isivuno sempendulo (Itheyibhile 1, iingeniso 16–18). Izifundo ezongezelelweyo zibonise ukuba amaqondo obushushu angaphantsi nangaphezulu kwama-60 °C awazange ayinyuse isivuno sempendulo (Itheyibhile 1, iingeniso 19 kunye nama-20). Xa umthwalo we-catalyst utshintshelwe kwi-2 kunye ne-10 mol %, isivuno besiyi-78% kunye ne-92%, ngokulandelelana (Itheyibhile 1, iingeniso 21 kunye nama-22). Isivuno sehlile xa impendulo yenziwa phantsi kwe-nitrogen atmosphere, nto leyo ebonisa ukuba i-oxygen esemoyeni inokudlala indima ebalulekileyo kwimpendulo (Itheyibhile 1, ingeniso 23). Ukwandisa ubungakanani be-ammonium acetate akuzange kuphucule iziphumo zempendulo kwaye kwanciphisa nesivuno (Itheyibhile 1, ingeniso 24 kunye ne-25). Ukongeza, akukho phuculo kwisivuno sempendulo esibonwe ngokwanda kwenani le-catechol (Itheyibhile 1, ingeniso 26).
Emva kokufumanisa iimeko ezifanelekileyo zokusabela, ukuguquguquka kunye nokusebenza kwempendulo kuye kwafundwa (Umfanekiso 3). Ekubeni ii-alkynes kunye nee-alkenes zinamaqela abalulekileyo asebenzayo kwi-organic synthesis kwaye kulula ukuzisebenzisa ngakumbi, ii-benzoxazole derivatives ezininzi zenziwe ngee-alkenes kunye nee-alkynes (4b–4d, 4f–4g). Kusetyenziswa i-1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde njenge-aldehyde substrate (4e), isivuno sifikelele kwi-90%. Ukongeza, ii-benzoxazoles ze-alkyl halo-substituted zenziwe ngeemveliso eziphezulu, ezinokusetyenziselwa ukubopha nezinye iimolekyuli kunye nokuveliswa ngakumbi (4h–4i) 52. I-4-((4-fluorobenzyl)oxy)benzaldehyde kunye ne-4-(benzyloxy)benzaldehyde zinike ii-benzoxazoles ezifanayo i-4j kunye ne-4k kwiimveliso eziphezulu, ngokulandelanayo. Sisebenzisa le ndlela, siphumelele ekuveliseni ii-benzoxazole derivatives (4l kunye ne-4m) eziqulethe i-quinolone moieties53,54,55. I-Benzoxazole 4n equlathe amaqela amabini e-alkyne yenziwe nge-84% yesivuno esivela kwi-benzaldehydes ezifakwe endaweni ye-2,4. I-Bicyclic compound 4o equlathe i-indole heterocycle yenziwe ngempumelelo phantsi kweemeko eziphuculweyo. I-Compound 4p yenziwe kusetyenziswa i-aldehyde substrate eqhotyoshelwe kwiqela le-benzonitrile, eliyi-substrate eluncedo ekulungiseleleni i-(4q-4r) supramolecules56. Ukuze sibonise ukusebenza kwale ndlela, ukulungiswa kwee-benzoxazole molecules eziqulethe i-β-lactam moieties (4q-4r) kuboniswe phantsi kweemeko eziphuculweyo nge-reaction ye-aldehyde-functionalized β-lactams, i-catechol, kunye ne-ammonium acetate. Ezi mvavanyo zibonisa ukuba indlela entsha yokwenziwa ingasetyenziselwa ukusebenza kwee-molecules ezintsonkothileyo kwisigaba samva nje.
Ukuze sibonise ngakumbi ukuguquguquka kunye nokunyamezelana kwale ndlela kumaqela asebenzayo, sifunde ii-aldehydes ezahlukeneyo ezinuka kamnandi kuquka amaqela anikela nge-electron, amaqela akhupha i-electron, ii-heterocyclic compounds, kunye nee-polycyclic aromatic hydrocarbons (Umfanekiso 4, 4s–4aag). Umzekelo, i-benzaldehyde yaguqulwa yaba yimveliso efunekayo (4s) kwi-92% yesivuno esisodwayo. Ii-aldehydes ezinuka kamnandi ezinamaqela anikela nge-electron (kuquka i--Me, i-isopropyl, i-tert-butyl, i-hydroxyl, kunye ne-para-SMe) zaguqulwa ngempumelelo zaba ziimveliso ezihambelanayo kwisivuno esihle kakhulu (4t–4x). Ii-substrates ze-aldehyde ezithintelwe yi-sterically zinokuvelisa iimveliso ze-benzoxazole (4y–4aa, 4al) kwisivuno esihle ukuya kwesigqwesileyo. Ukusetyenziswa kwe-benzaldehydes ezifakwe endaweni ye-meta (4ab, 4ai, 4am) kwavumela ukulungiswa kweemveliso ze-benzoxazole kwisivuno esiphezulu. Ii-aldehydes zeHalogenated ezifana ne-(-F, -CF3, -Cl kunye ne-Br) zinike ii-benzoxazoles ezifanelekileyo (4af, 4ag kunye ne-4ai-4an) kwisivuno esaneleyo. Ii-Aldehydes ezinamaqela okutsala ii-electron (umz. -CN kunye ne-NO2) nazo zasabela kakuhle kwaye zanika iimveliso ezifunwayo (4ah kunye ne-4ao) kwisivuno esiphezulu.
Uthotho lweempendulo ezisetyenziselwa ukwenziwa kwee-aldehydes a kunye ne-b. a Iimeko zempendulo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) kunye ne-ZrCl4 (5 mol%) zaphendulwa kwi-EtOH (3 mL) kwi-60 °C kangangeeyure ezi-6. b Isivuno sihambelana nemveliso ehlukanisiweyo.
Ii-polycyclic aromatic aldehydes ezifana ne-1-naphthaldehyde, i-anthracene-9-carboxaldehyde kunye ne-phenanthrene-9-carboxaldehyde zinokuvelisa iimveliso ezifunwayo ze-4ap-4ar kwisivuno esiphezulu. Ii-heterocyclic aromatic aldehydes ezahlukeneyo kuquka i-pyrrole, i-indole, i-pyridine, i-furan kunye ne-thiophene zikwazile ukumelana neemeko zokusabela kakuhle kwaye zinokuvelisa iimveliso ezifanelekileyo (4as-4az) kwisivuno esiphezulu. I-Benzoxazole 4aag ifunyenwe kwisivuno se-52% kusetyenziswa i-aliphatic aldehyde efanelekileyo.
Indawo yempendulo esebenzisa i-aldehydes yorhwebo a, b. a Iimeko zempendulo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) kunye ne-ZrCl4 (5 mol %) ziphenduliwe kwi-EtOH (5 mL) kwi-60 °C kangangeeyure ezi-4. b Isivuno sihambelana nemveliso ehlukanisiweyo. c Impendulo yenziwe kwi-80 °C kangangeeyure ezi-6; d Impendulo yenziwe kwi-100 °C kangangeeyure ezingama-24.
Ukuze sibonise ngakumbi ukuguquguquka nokusebenza kwale ndlela, sikwavavanye ii-catechol ezahlukeneyo ezitshintshiweyo. Ii-catechol ezitshintshiweyo nge-monosubstituted ezifana ne-4-tert-butylbenzene-1,2-diol kunye ne-3-methoxybenzene-1,2-diol zasabela kakuhle kule protocol, zinika ii-benzoxazoles i-4aaa–4aac kwi-89%, 86%, kunye ne-57% isivuno, ngokwahlukeneyo. Ezinye ii-benzoxazoles ezitshintshiweyo nge-polysubstituted nazo zenziwe ngempumelelo kusetyenziswa ii-catechols ezitshintshiweyo nge-polysubstituted ezifanelekileyo (4aad–4aaf). Akukho mveliso ifunyenweyo xa kusetyenziswa ii-catechol ezitshintshiweyo ezingena-electron ezifana ne-4-nitrobenzene-1,2-diol kunye ne-3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
Ukwenziwa kwe-benzoxazole kwiigram kwenziwa ngempumelelo phantsi kweemeko ezilungisiweyo, kwaye i-compound 4f yenziwe nge-85% yesivuno esizimeleyo (Umfanekiso 5).
Ukwenziwa kwe-benzoxazole 4f ngegram-scale. Iimeko zokusabela: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) kunye ne-ZrCl4 (5 mol%) zisabela kwi-EtOH (25 mL) kwi-60 °C kangangeeyure ezi-4.
Ngokusekelwe kwidatha yoncwadi, kuye kwacetyiswa indlela efanelekileyo yokusabela yokwenza i-benzoxazoles kwi-catechol, i-aldehyde, kunye ne-ammonium acetate phambi kwe-ZrCl4 catalyst (Umfanekiso 6). I-Catechol ingayitshintsha i-zirconium ngokudibanisa amaqela amabini e-hydroxyl ukwenza isiseko sokuqala somjikelo we-catalytic (I)51. Kule meko, i-semiquinone moiety (II) inokwenziwa nge-enol-keto tautomerization kwi-complex I58. Iqela le-carbonyl elenziwe kwi-intermediate (II) ngokubonakalayo lisabela ne-ammonium acetate ukwenza i-intermediate imine (III) 47. Enye into enokwenzeka kukuba i-imine (III^), eyenziwe yi-reaction ye-aldehyde kunye ne-ammonium acetate, isabela neqela le-carbonyl ukwenza i-intermediate imine-phenol (IV) 59,60. Emva koko, i-intermediate (V) ingadlula kwi-intramolecular cyclization40. Okokugqibela, i-intermediate V ixutywa ne-oxygen esemoyeni, ivelise imveliso efunekayo 4 kwaye ikhuphe i-zirconium complex ukuqala umjikelo olandelayo 61,62.
Zonke ii-reagents kunye nezinyibilikisi zithengwe kwimithombo yorhwebo. Zonke iimveliso ezaziwayo zichongiwe ngokuthelekisa idatha ye-spectral kunye neendawo zokunyibilika zeesampuli ezivavanyiweyo. Ii-spectra ze-1H NMR (400 MHz) kunye ne-13C NMR (100 MHz) zirekhodwe kwisixhobo seBrucker Avance DRX. Iindawo zokunyibilika zichongiwe kwisixhobo seBüchi B-545 kwi-capillary evulekileyo. Zonke ii-reaction zijongwe yi-thin-layer chromatography (TLC) kusetyenziswa iiplate ze-silica gel (Silica gel 60 F254, Merck Chemical Company). Uhlalutyo lwe-elemental lwenziwe kwi-PerkinElmer 240-B Microanalyzer.
Isisombululo se-catechol (1.0 mmol), i-aldehyde (1.0 mmol), i-ammonium acetate (1.0 mmol) kunye ne-ZrCl4 (5 mol %) kwi-ethanol (3.0 mL) savuselelwa ngokulandelelana kwityhubhu evulekileyo kwindawo yokuhlamba ioyile kwi-60 °C phantsi komoya ixesha elifunekayo. Inkqubela phambili yempendulo yajongwa yi-thin layer chromatography (TLC). Emva kokugqitywa kwempendulo, umxube ophumayo wapholiswa ukuya kubushushu begumbi kwaye i-ethanol yasuswa phantsi koxinzelelo oluphantsi. Umxube wempendulo waxutywa ne-EtOAc (3 x 5 mL). Emva koko, iileya ezidityanisiweyo ze-organic zomiswa phezu kwe-Na2SO4 engenamanzi zaza zagxininiswa kwi-vacuo. Ekugqibeleni, umxube ongcolileyo wacocwa yi-column chromatography kusetyenziswa i-petroleum ether/EtOAc njenge-eluent yokufumana i-benzoxazole ecocekileyo 4.
Ngamafutshane, siphuhlise iprotokholi entsha, ethambileyo neluhlaza yokwenza i-benzoxazoles ngokwenziwa ngokulandelelana kwe-CN kunye ne-CO bonds phambi kwe-zirconium catalyst. Phantsi kweemeko zokusabela ezilungiselelweyo, kwenziwa i-benzoxazoles ezahlukeneyo ezingama-59. Iimeko zokusabela ziyahambelana namaqela ahlukeneyo asebenzayo, kwaye ii-cores ezininzi ezisebenzayo zenziwe ngempumelelo, nto leyo ebonisa amandla azo aphezulu okusebenza okulandelayo. Ke ngoko, siphuhlise icebo elisebenzayo, elilula nelisebenzayo lokuvelisa ngokubanzi izinto ezahlukeneyo ze-benzoxazole ezivela kwii-catechol zendalo phantsi kweemeko eziluhlaza kusetyenziswa ii-catalysts ezingabizi kakhulu.
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