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Irhubhululo leli libika indlela esebenza kuhle khulu yokwenza ama-benzoxazoles kusetjenziswa i-catechol, i-aldehyde kanye ne-ammonium acetate njenge-feedstock ngokusebenzisa ukusabela kokuhlanganisa ku-ethanol nge-ZrCl4 njenge-catalyst. Uchungechunge lwama-benzoxazoles (imihlobo ema-59) lwakhiwa ngempumelelo ngalendlela ngokukhiqiza okufika ku-97%. Ezinye iinzuzo zendlela le zifaka hlangana ukuhlanganiswa okukhulu nokusetjenziswa kwe-oksijini njenge-ejenti ye-oksijini. Ubujamo bokuphendula obulula buvumela ukusebenza okulandelako, okwenza bona kube lula ukuhlanganiswa kwezinto ezihlukahlukeneko ezinezakhiwo ezihlobene nezinto eziphilako ezifana nama-β-lactams kanye nama-quinoline heterocycles.
Ukuthuthukiswa kweendlela ezitjha zokuhlanganiswa kwezinto eziphilako ezingaqeda ukulinganiselwa kokuthola amakhompawundi wezinga eliphezulu begodu kwandise ukuhlukahluka kwawo (ukuvula iindawo ezitjha ezingaba khona zokusetjenziswa) kudose ukutjhejwa okukhulu kokubili eemfundweni nezebubulweni1,2. Ngaphezu kokusebenza kuhle kwalezi zindlela, ukungabi nobungani kwebhoduluko kweendlela ezithuthukiswako nakho kuzokuba yinzuzo ekulu3,4.
Ama-benzoxazoles mhlobo wamakhompawundi we-heterocyclic adose ukutjhejwa okukhulu ngebanga lemisebenzi yawo enengi yezinto eziphilako. Amakhompawundi anjalo abikwe bona anemisebenzi yokulwa namagciwani, ukuvikela imizwa, ukulwa nomdlavuza, ukulwa namagciwane, ukulwa namagciwane, ukulwa nama-fungal, nokulwa nokuvuvuka5,6,7,8,9,10,11. Zisetjenziswa khulu emikhakheni ehlukahlukeneko yezebubulo efakahlangana imithi, iinzwa, i-agrochemistry, ama-ligand (we-transition metal catalysis), kanye nesayensi yezinto12,13,14,15,16,17. Ngebanga lezakhiwo zawo ezihlukileko zamakhemikhali nokusetjenziswa kwazo, ama-benzoxazoles sele aba zizinto eziqakathekileko zokwakha ukwakheka kwamamolekhyuli amanengi ahlangahlangeneko18,19,20. Ngokuthakazelisako, amanye ama-benzoxazoles ayimikhiqizo yemvelo eqakathekileko begodu amamolekhyuli afaneleko wezokwelapha, afana ne-nakijinol21, i-boxazomycin A22, i-calcimycin23, i-tafamidis24, i-cabotamycin25 kanye ne-neosalvianene (Umfanekiso 1A)26.
(A) Iimbonelo zemikhiqizo yemvelo esekelwe ku-benzoxazole kanye namakhompawundi asebenzako. (B) Eminye imithombo yemvelo yama-catechols.
Ama-Catechol asetjenziswa khulu emikhakheni eminengi njengemithi, izimonyo kanye nesayensi yezinto ezisetjenziswako27,28,29,30,31. Ama-Catechol nawo atjengiswe bona anezinto ezilwa nokuvuvuka, okwenza bona abe ziinsetjenziswa zokwelapha32,33. Ipahla le irholele ekusetjenzisweni kwayo ekuthuthukisweni kwemikhiqizo yokuzilungisa yokulwisana nokuguga nemikhiqizo yokutlhogomela isikhumba34,35,36. Ukudlula lapho, ama-catechols atjengiswe njengeenqalo eziphumelelako zokwakheka kwezinto eziphilako (Umfanekiso 1B)37,38. Amanye wama-catechols la anengi khulu emvelweni. Ngalokho-ke, ukusetjenziswa kwayo njengesisetjenziswa esingakalungiswa nofana isisetjenziswa sokuthoma sokwenza izinto eziphilako kungafaka hlangana umthetho wekhemistri ohlaza "wokusebenzisa iinsetjenziswa ezivuselelekako". Iindlela ezinengi ezihlukahlukeneko zithuthukiswe ukulungiselela amakhompawundi we-benzoxazole asebenzako7,39. Ukusebenza kwe-oxidative kwe-C(aryl)-OH bond yama-catechols ngenye yeendlela ezikarisako nezitjha zokwakha ama-benzoxazoles. Iimbonelo zalendlela ekuhlanganisweni kwama-benzoxazoles kukuphendula kwama-catechols nama-amines40,41,42,43,44, nama-aldehydes45,46,47, nama-alcohols (nofana ama-ethers)48, kanye nama-ketones, ama-alkenes nama-alkynes (Umfanekiso 2A)49. Kulesi sifundo, ukusabela okuneengcenye ezinengi (i-MCR) hlangana ne-catechol, i-aldehyde kanye ne-ammonium acetate kwasetjenziselwa ukwakheka kwama-benzoxazoles (Umfanekiso 2B). Ukusabela kwenziwa kusetjenziswa inani elikhuthazako le-ZrCl4 ku-ethanol solvent. Tjheja bona i-ZrCl4 ingathathwa njenge-green Lewis acid catalyst, yi-compound enganabuthi [LD50 (ZrCl4, oral for rats) = 1688 mg kg−1] begodu ayithathwa njengenobuthi obukhulu50. Ama-catalyst we-zirconium nawo asetjenziswe ngepumelelo njengama-catalyst wokuhlanganiswa kwamakhompawundi ahlukahlukeneko we-organic. Iindleko zazo eziphasi nokuzinza kwazo okuphezulu emanzini ne-oksijini kwenza bona zibe ziinkhuthazi ezithembisako ekukhiqizeni izinto eziphilako51.
Ukuthola ubujamo obufaneleko bokuphendula, sikhethe i-3,5-di-tert-butylbenzene-1,2-diol 1a, i-4-methoxybenzaldehyde 2a kanye netswayi le-ammonium 3 njengeendlela zokuphendula begodu senza ukuphendula phambi kwama-Lewis acid ahlukileko (LA), iinsombululo ezihlukileko kanye namazinga womtjhiso we-benxazezole (44 1). Akukho mkhiqizo owabonwa ngokungabi khona kwe-catalyst (Ithebula 1, ukungena 1). Ngemva kwalokho, i-5 mol % yama-esidi we-Lewis ahlukileko afana ne-ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 kanye ne-MoO3 zahlolwa njengeentjhukumisi ku-EtOH solvent begodu i-ZrCl4 yatholakala ingcono khulu (Ithebula 1–28 entries). Ukuthuthukisa ukusebenza kuhle, iinsombululo ezihlukahlukeneko zahlolwa ezifaka hlangana i-dioxane, i-acetonitrile, i-ethyl acetate, i-dichloroethane (DCE), i-tetrahydrofuran (THF), i-dimethylformamide (DMF) kanye ne-dimethyl sulfoxide (DMSO). Iinthelo zazo zoke iinsombululo ezihloliweko bezingaphasi kwe-ethanol (Ithebula 1, ukufakwa 9-15). Ukusebenzisa eminye imithombo ye-nitrogen (njenge-NH4Cl, NH4CN kanye (NH4)2SO4) esikhundleni se-ammonium acetate akuzange kwenze ngcono ukukhiqizwa kokusabela (Ithebula 1, ukufakwa 16–18). Iimfundo ezilandelako zitjengise bona amazinga womtjhiso angaphasi nangaphezulu kwama-60 °C azange akhuphule isivuno sokuphendula (Ithebula 1, ukungena 19 no-20). Lokha ukulayisha kwe-catalyst nakutjhugululwa kwaba yi-2 kanye ne-10 mol %, ukukhiqiza bekungu-78% no-92%, ngokulandelana (Ithebula 1, ukungena 21 no-22). Isivuno sehla lokha ukusabela kwenziwa ngaphasi komkhathi we-nitrogen, okutjengisa bona i-oksijini yommoya ingadlala indima eqakathekileko ekusabeleni (Ithebula 1, ukungena 23). Ukukhuphula inani le-ammonium acetate akuzange kwenze ngcono imiphumela yokusabela begodu kwehlise isivuno (Ithebula 1, ukufakwa 24 no-25). Ukungezelela, akukho ukuthuthuka ekukhiqizweni kokuphendula okwabonwa ngokukhuphula inani le-catechol (Ithebula 1, ukungena 26).
Ngemva kokuthola ubujamo obuhle bokuphendula, ukuhlukahluka nokusetjenziswa kokuphendula kwafundwa (Umfanekiso 3). Njengombana ama-alkynes nama-alkenes anamaqembu asebenzako aqakathekileko ekukhiqizweni kwezinto eziphilako begodu alula ukwamukelwa, ama-benzoxazole amanengi akhiqizwa ngama-alkenes nama-alkynes (4b–4d, 4f–4g). Ukusebenzisa i-1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde njenge-aldehyde substrate (4e), isivuno sifike ku-90%. Ukungezelela, ama-alkyl halo-substituted benzoxazoles akhiwe ngezivuno eziphezulu, ezingasetjenziselwa ukuhlanganisa namanye amamolekhyuli nokuragela phambili nokukhiqiza (4h–4i) 52. isivuno, ngokulandelana. Ngokusebenzisa indlela le, siphumelele ukwenza ama-benzoxazole derivatives (4l no-4m) aneengcenye ze-quinolone53,54,55. I-Benzoxazole 4n equkethe amaqembu amabili we-alkyne yenziwa nge-84% yokukhiqiza ukusuka kuma-benzaldehydes afakwe ama-2,4. I-bicyclic compound 4o equkethe i-indole heterocycle yenziwa ngempumelelo ngaphasi kweemeko ezihlelekileko. Ikhompawundi 4p yenziwa kusetjenziswa i-aldehyde substrate enamathele ku-benzonitrile group, okuyi-substrate ewusizo ekulungiseleleni (4q-4r) supramolecules56. Ukuveza ukusetjenziswa kwalendlela, ukulungiselela amamolekhuli we-benzoxazole ane-β-lactam moieties (4q–4r) kwatjengiswa ngaphasi kweemeko ezihlelekileko ngokusebenzisa ukusabela kwe-aldehyde-functionalized β-lactams, catechol, kanye ne-ammonium acetate. Iimhloliso lezi zitjengisa bona indlela etja yokwenza izinto ingasetjenziselwa ukusebenza kwesigaba sokugcina samamolekhyuli ahlangahlangeneko.
Ukuragela phambili nokutjengisa ukusetjenziswa nokubekezelelana kwalendlela emaqenjini asebenzako, sifunde ama-aldehyde ahlukahlukeneko anephunga elifaka hlangana amaqembu anikela nge-elekthronikhi, amaqembu akhipha i-elekthronikhi, amakhompawundi we-heterocyclic, kanye nama-hydrocarbon we-polycyclic (Umfanekiso 4, 4s–4aag). Ukwenza isibonelo, i-benzaldehyde yatjhugululwa yaba mkhiqizo ofunekako (4s) nge-92% yesivuno esihlukileko. Ama-aldehyde anephunga elinamaqembu anikela nge-elekthronikhi (okufaka hlangana i-Me, isopropyl, i-tert-butyl, i-hydroxyl, kanye ne-para-SMe) atjhugululwa ngempumelelo abe mikhiqizo ehambelana nayo ngemiphumela emihle khulu (4t–4x). Ama-substrate we-aldehyde avinjelwe khulu angakhiqiza imikhiqizo ye-benzoxazole (4y–4aa, 4al) ngemikhiqizo emihle ukuya emihle khulu. Ukusetjenziswa kwama-meta-substituted benzaldehydes (4ab, 4ai, 4am) kwavumela ukulungiselela imikhiqizo ye-benzoxazole ngezivuno eziphezulu. Ama-aldehyde ane-halogen afana ne-(-F, -CF3, -Cl kanye ne-Br) anikela ama-benzoxazoles ahambelanako (4af, 4ag kanye ne-4ai-4an) ngesivuno esanelisako. Ama-aldehyde aneenqhema ezikhipha i-elekthronikhi (isib. -CN ne-NO2) nawo asabela kuhle begodu anikela ngemikhiqizo efunwako (4ah ne-4ao) ngesivuno esiphezulu.
Uchungechunge lokusabela olusetshenziselwa ukwakheka kwama-aldehyde a no-b. a Iimeko zokuphendula: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) kanye ne-ZrCl4 (5 mol%) zaphendulwa ku-EtOH (3 mL) ku-60 °C ama-awa asithandathu. b Isivuno sihambisana nomkhiqizo ohlukanisiweko.
Ama-aldehyde we-polycyclic aromatic afana ne-1-naphthaldehyde, i-anthracene-9-carboxaldehyde kanye ne-phenanthrene-9-carboxaldehyde angakhiqiza imikhiqizo efunwako 4ap-4ar ngesivuno esiphezulu. Ama-aldehyde ahlukahlukeneko we-heterocyclic aromatic afakahlangana i-pyrrole, i-indole, i-pyridine, i-furan kanye ne-thiophene abekezelela kuhle ubujamo bokuphendula begodu angakhiqiza imikhiqizo ehambelana nayo (4as-4az) ngesivuno esiphezulu. I-Benzoxazole 4aag yatholwa nge-52% kusetjenziswa i-aliphatic aldehyde.
Indawo yokuphendula isebenzisa ama-aldehyde wokuthengisa a, b. a Iimeko zokuphendula: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) kanye ne-ZrCl4 (5 mol %) zaphendulwa ku-EtOH (5 mL) ku-60 °C ama-awa ama-4. b Isivuno sihambisana nomkhiqizo ohlukanisiweko. c Ukusabela kwenziwa ku-80 °C ama-awa asithandathu; d Ukusabela kwenziwa ku-100 °C ama-awa ama-24.
Ukuragela phambili nokutjengisa ukusetjenziswa nokusetjenziswa kwalendlela, sibuye sahlola ama-catechols ahlukahlukeneko afakwe esikhundleni. Ama-catechol afakwe indawo eyodwa afana ne-4-tert-butylbenzene-1,2-diol kanye ne-3-methoxybenzene-1,2-diol asabela kuhle ngale phrothokholi, anikela ama-benzoxazoles 4aaa–4aac ngama-89%, 86%, kanye nama-57%, ngokulandelana. Amanye ama-benzoxazoles ahlanganisiweko nawo akhiwe ngepumelelo kusetjenziswa ama-catechols ahlanganisiweko (4aad–4aaf). Akukho mikhiqizo eyatholwa lokha nakusetjenziswa ama-catechols afakwe nge-elekthronikhi afana ne-4-nitrobenzene-1,2-diol kanye ne-3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
Ukuhlanganiswa kwe-benzoxazole ngobunengi bamagremu kwafezwa ngepumelelo ngaphasi kwemibandela ehlelekileko, begodu i-compound 4f yenziwa nge-85% yesivuno esihlukileko (Umfanekiso 5).
Ukuhlanganiswa kwe-gram-scale ye-benzoxazole 4f. Ubujamo bokuphendula: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) kanye ne-ZrCl4 (5 mol%) kwaphendulwa ku-EtOH (25 mL) ku-60 °C ama-awa ama-4.
Ngokuya ngedatha yemitlolo, indlela yokuphendula ezwakalako ihlongozwe ukwakhiwa kwama-benzoxazoles avela ku-catechol, i-aldehyde, kanye ne-ammonium acetate ebukhoneni be-ZrCl4 catalyst (Umfanekiso 6). I-Catechol ingakhipha i-zirconium ngokuhlanganisa amaqembu amabili we-hydroxyl ukwakha umgogodla wokuthoma womjikelezo we-catalytic (I)51. Kulokhu, i-semiquinone moiety (II) ingabunjwa nge-enol-keto tautomerization ku-complex I58. Isiqhema se-carbonyl esakhiwe ku-intermediate (II) kubonakala ngasuthi sisebenzisana ne-ammonium acetate ukwakha i-intermediate imine (III) 47. Okunye okungenzeka kukobana i-imine (III^), eyakhiwe ngokusabela kwe-aldehyde ne-ammonium acetate, isabelana ne-carbonyl group ukwakha i-intermediate imine-phenol (IV) 47, 56 . Ngemva kwalokho, okuphakathi (V) kungathola ukujikeleziswa kwangaphakathi kwamamolekhyuli40. Ekugcineni, i-V ephakathi i-oksijini nge-oksijini yomkhathi, ikhiqize umkhiqizo ofunekako 4 begodu ikhuphe i-zirconium complex ukuthoma umjikelezo olandelako61,62.
Zoke ii-reagents kanye ne-solvents zithengwe emithonjeni yezokurhweba. Yonke imikhiqizo eyaziwako ikhonjwe ngokumadanisa idatha ye-spectral kanye namaphuzu wokuncibilika wamasampula ahloliweko. I-1H NMR (400 MHz) kanye ne-13C NMR (100 MHz) i-spectra yarekhodwa ngesisetjenziswa se-Brucker Avance DRX. Amaphuzu wokuncibilika atholakala ku-Büchi B-545 nge-apharathasi evulekileko. Zoke iindlela zokuphendula zagadwa nge-thin-layer chromatography (TLC) kusetjenziswa amapuleti we-silica gel (i-Silica gel 60 F254, i-Merck Chemical Company). Ukuhlaziywa kwezinto kwenziwa ku-PerkinElmer 240-B Microanalyzer.
Isisombululo 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) yavuselelwa ngokulandelana ngaphakathi kwetjhubhu evulekileko ngaphakathi kwe-oyili ebhathini ku-60 °C ngaphasi komoya isikhathi esitlhogekako. Ukuragela phambili kokuphendula kwabekwa ilihlo nge-thin layer chromatography (TLC). Ngemva kokuqeda ukusabela, ingxube ephumelako yapholiswa yaba sezingeni lokushisa legumbi begodu i-ethanol yasuswa ngaphasi komfutho ophasi. Umxube wokusabela wahlanjululwa nge-EtOAc (3 x 5 mL). Bese, amalayini we-organic ahlanganisiweko omiswa phezu kwe-Na2SO4 enganamanzi begodu ahlanganiswa ngaphakathi kwe-vacuo. Ekugcineni, ingxube ehlanzekileko yahlanjululwa nge-kholomu chromatography kusetjenziswa i-petroleum ether/EtOAc njenge-eluent ukuthola i-benzoxazole 4 ehlanzekileko.
Ngokufingqa, sithuthukise iphrothokholi etja, elula nehlaza yokwenza ama-benzoxazoles ngokusebenzisa ukwakheka okulandelanako kwamabhondi we-CN ne-CO ebukhoneni be-zirconium catalyst. Ngaphasi kwemibandela yokusabela ehlelekileko, kwakhiwa ama-benzoxazoles ahlukileko ama-59. Ubujamo bokuphendula buhambisana namaqembu ahlukahlukeneko asebenzako, begodu ama-cores amanengi aphilako akhiwe ngepumelelo, okutjengisa amandla wawo aphezulu wokusebenza okulandelako. Ngalokho-ke, sithuthukise isu elisebenzako, elilula nelisebenzako lokukhiqiza ngezinga elikhulu lama-benzoxazole ahlukahlukeneko avela kuma-catechol wemvelo ngaphasi kwemibandela eluhlaza sisebenzisa ama-catalyst abiza kancani.
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