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Dyondzo leyi yi vika ndlela leyi tirhaka swinene eka ku endliwa ka ti benzoxazoles hiku tirhisa catechol, aldehyde na ammonium acetate tani hi swakudya hiku tirhisa coupling reaction eka ethanol na ZrCl4 tani hi catalyst. Nxaxamelo wa ti benzoxazoles (59 wa tinxaka) wu endliwile hiku humelela hi ndlela leyi eka mbuyelo wofika eka 97%. Swipfuno swin’wana swa endlelo leri swikatsa ku hlanganisiwa lokukulu na kutirhisiwa ka oxygen tani hi oxidizing agent. Swiyimo swa mild reaction swipfumelela functionalization leyi landzelaka, leswi olovisaka ku endliwa ka ti derivatives to hambana hambana letingana swivumbeko leswi fambelanaka na biologically swofana na β-lactams na quinoline heterocycles.
Ku tumbuluxiwa ka tindlela tintshwa ta organic synthesis leti nga hlulaka swipimelo eka ku kuma swihlanganisi swa nkoka wa le henhla na ku engetela ku hambana ka swona (ku pfula tindhawu letintshwa leti nga na vuswikoti byo tirhisiwa) swi koke nyingiso lowukulu eka tidyondzo na indasitiri1,2. Ku engetela eka vukorhokeri bya le henhla bya maendlelo lawa, ku va na xinghana na mbango ka maendlelo lama tumbuluxiwaka na swona swi ta va vuyelo lebyikulu3,4.
Benzoxazoles i ntlawa wa ti heterocyclic compounds letinga koka rinoko swinene hikokwalaho ka migingiriko ya tona yo fuwa ya biological. Swihlanganisi swo tano swi vikiwile ku va na migingiriko ya antimicrobial, neuroprotective, anticancer, antiviral, antibacterial, antifungal, na anti-inflammatory activities5,6,7,8,9,10,11. Titlhela titirhisiwa ngopfu eka tinsimu tohambana hambana ta ti indasitiri kukatsa na mirhi, sensorics, agrochemistry, ligands (for transition metal catalysis), na sayense ya switirhisiwa12,13,14,15,16,17. Hikwalaho ka swivumbeko swa tona swo hlawuleka swa tikhemikhali na ku tirhisiwa ko tala, ti benzoxazoles ti hundzuke swiaki swa nkoka eka ku endliwa ka ti molecule to tala to rharhangana ta organic18,19,20. Lexi tsakisaka, ti benzoxazoles tin’wana i switirhisiwa swa nkoka swa ntumbuluko na ti molecules leti fambelanaka na pharmacologically, kufana na nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 na neosalvianene (Xifaniso 1A)26.
(A) Swikombiso swa switirhisiwa swa ntumbuluko leswi simekiweke eka benzoxazole na swihlanganisi swa bioactive. (B) Swihlovo swin’wana swa ntumbuluko swa ti- catechol.
Ti catechol ti tirhisiwa ngopfu eka tinsimu to tala to fana na mirhi, switolwa na sayense ya switirhisiwa27,28,29,30,31. Ti catechols titlhele ti kombisiwa kuva tiri na switirhisiwa swa antioxidant na anti-inflammatory, leswi endlaka leswaku tiva ti candidates tani hi switirhisiwa swa vutshunguri32,33. Nhundzu leyi yi endle leswaku yi tirhisiwa eka ku tumbuluxiwa ka switolwa swo lwisana na ku dyuhala na switirhisiwa swo hlayisa nhlonge34,35,36. Kuya emahlweni, ti catechols ti kombisiwile kuva tiri ti precursors leti tirhaka eka organic synthesis (Figure 1B)37,38. Tin’wana ta ti- catechol leti ti tele ngopfu hi ntumbuluko. Hikokwalaho, kutirhisiwa ka yona tani hi raw material kumbe masungulo ya organic synthesis swinga katsa green chemistry principle ya “utilizing renewable resources”. Tindlela to hlaya to hambana ti tumbuluxiwile ku lulamisa swihlanganisi swa benzoxazole leswi tirhaka7,39. Oxidative functionalization ya C(aryl)-OH bond ya ti catechols i yin’wana ya maendlelo yo tsakisa swinene na ya novhele eka ku endliwa ka ti benzoxazoles. Swikombiso swa endlelo leri eka ku hlanganisiwa ka ti benzoxazoles i ku cinca ka ti catechols na ti amines40,41,42,43,44, na ti aldehydes45,46,47, na ti alcohols (kumbe ti ethers)48, xikan’we na ti ketones, alkenes na alkynes (Xifaniso 2A)49. Eka ndzavisiso lowu, ku tirhisiwile multicomponent reaction (MCR) exikarhi ka catechol, aldehyde na ammonium acetate eka ku endliwa ka ti benzoxazoles (Xifaniso 2B). Ku cinca cinca loku ku endliwile hiku tirhisa nhlayo ya catalytic ya ZrCl4 eka ethanol solvent. Xiya leswaku ZrCl4 yinga tekiwa tani hi rihlaza ra Lewis acid catalyst, i nkatsakanyo lowu nga riki na chefu ngopfu [LD50 (ZrCl4, oral for rats) = 1688 mg kg−1] naswona ayi tekiwi tani hi chefu swinene50. Ti zirconium catalysts titlhele titirhisiwa hiku humelela tani hi ti catalysts eka ku endliwa ka ti organic compounds tohambana hambana. Ntsengo wa tona wa le hansi na ku tshamiseka ka tona lokukulu eka mati na okisijini swi endla leswaku ti va ti catalysts leti tshembisaka eka organic synthesis51.
Ku kuma swiyimo leswi faneleke swa reaction, hi hlawurile 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a na ammonium salt 3 tani hi model reactions naswona hi endle reactions eka vukona bya ti Lewis acids to hambana (LA), ti solvents to hambana na mahiselo ku endla benzoxazole 4a (Table 1). Ku hava xiendliwa lexi voniweke eka ku pfumaleka ka catalyst (Table 1, entry 1). Endzhaku ka sweswo, 5 mol % ya ti Lewis acids tohambana hambana tofana na ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 na MoO3 ti kamberiwile tani hi ti catalysts eka EtOH solvent naswona ZrCl4 yikumeke yiri ya kahle swinene (Table 1, entries 2–8). Ku antswisa vukorhokeri, swintshuxekisi swohambana hambana swikamberiwile kukatsa na dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) na dimethyl sulfoxide (DMSO). Mbuyelo wa ti solvents hinkwato leti kamberiweke atiri ehansi kutlula ta ethanol (Table 1, entries 9–15). Ku tirhisa swihlovo swin’wana swa nitrogen (kufana na NH4Cl, NH4CN na (NH4)2SO4) ematshan’wini ya ammonium acetate aswi antswisanga mbuyelo wa reaction (Table 1, entries 16–18). Mindzavisiso yin’wana yi kombisile leswaku mahiselo yale hansi nale henhla ka 60 °C aya antswisi mbuyelo wa reaction (Table 1, entries 19 na 20). Loko catalyst loading yi cinciwile kuya eka 2 na 10 mol %, mbuyelo awuri 78% na 92%, hiku landzelelana (Table 1, entries 21 na 22). Mbuyelo wuhunguteke loko reaction yi endliwile ehansi ka nitrogen atmosphere, leswi kombaka leswaku oxygen ya le xibakabakeni yinga tlanga xiave xa nkoka eka reaction (Table 1, entry 23). Ku engetela nhlayo ya ammonium acetate aswi antswisanga mbuyelo wa reaction naswona swihungute hambi kuri mbuyelo (Table 1, entries 24 na 25). Ku engetela kwalano, akuri hava ku antswisiwa eka mbuyelo wa reaction lowu voniweke hiku engetela nhlayo ya catechol (Table 1, entry 26).
Endzhaku ko kumisisa swiyimo swa kahle swa reaction, ku cinca cinca na ku tirhisiwa ka reaction swikamberiwile (Figure 3). Leswi ti alkynes nati alkenes tingana mintlawa ya nkoka ya ntirho eka organic synthesis naswona swi olovaka ku amukeleka eka ku ya emahlweni derivatization, ti benzoxazole derivatives to hlaya ti endliwile na ti alkenes na ti alkynes (4b–4d, 4f–4g). Hiku tirhisa 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde tani hi substrate ya aldehyde (4e), mbuyelo wufikelele 90%. Ku engetela kwalano, ti alkyl halo-substituted benzoxazoles ti endliwile hi mbuyelo wale henhla, leswinga tirhisiwaka eka ligation na ti molecules tin’wana xikan’we naku ya emahlweni derivatization (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde na 4-(benzyloxy)benzaldehyde swinyikile ti benzoxazoles leti fambelanaka 4j na 4k eka xiyimo xale henhla mbuyelo, hi ku landzelelana. Hi ku tirhisa ndlela leyi, hi humelerile ku endla swiaki swa benzoxazole (4l na 4m) leswi nga na swiphemu swa quinolone53,54,55. Benzoxazole 4n leyingana mintlawa yimbirhi ya alkyne yi endliwile hi mbuyelo wa 84% kusuka eka 2,4-substituted benzaldehydes. Bicyclic compound 4o leyingana indole heterocycle yi endliwile hiku humelela ehansi ka swiyimo leswi antswisiweke. Compound 4p yi endliwile hiku tirhisa substrate ya aldehyde leyi khomanisiweke na ntlawa wa benzonitrile, leyi nga substrate leyi pfunaka eka ku lulamisela (4q-4r) supramolecules56. Ku kombisa ku tirhisiwa ka ndlela leyi, ku lulamisiwa ka ti molecule ta benzoxazole letingana swiphemu swa β-lactam (4q–4r) swikombisiwile ehansi ka swiyimo leswi antswisiweke hiku tirhisa ku cinca ka aldehyde-functionalized β-lactams, catechol, na ammonium acetate. Swikambelo leswi swi kombisa leswaku endlelo lerintshwa leri tumbuluxiweke ra synthetic ri nga tirhisiwa eka late-stage functionalization ya ti molecules leti rharhanganeke.
Ku ya emahlweni hi kombisa ku cinca-cinca na ku tiyisela ka ndlela leyi eka mintlawa leyi tirhaka, hi dyondze hi ti aldehydes to hambana ta nun’hwelo ku katsa na mintlawa leyi nyikelaka tielektroni, mintlawa leyi hoxaka tielektroni, swihlanganisi swa heterocyclic, na tihayidirokhaboni to nun’hwela ta polycyclic (Xifaniso 4, 4s–4aag). Xikombiso, benzaldehyde yi hundzuriwile kuva xitirhisiwa lexi lavekaka (4s) eka 92% wa mbuyelo lowu hambanisiweke. Ti aromatic aldehydes letingana mintlawa leyi nyikaka ti electron (kukatsa na -Me, isopropyl, tert-butyl, hydroxyl, na para-SMe) ti hundzuriwile hiku humelela eka switirhisiwa leswi fambelanaka eka mbuyelo wa kahle swinene (4t–4x). Ti substrates ta aldehyde leti siveleriweke hi sterical tinga humesa switirhisiwa swa benzoxazole (4y–4aa, 4al) eka mbuyelo wa kahle kuya eka wa kahle swinene. Ku tirhisiwa ka meta-substituted benzaldehydes (4ab, 4ai, 4am) swipfumelele ku lulamisiwa ka switirhisiwa swa benzoxazole eka mbuyelo wale henhla. Ti halogenated aldehydes tofana na (-F, -CF3, -Cl na Br) tinyikile ti benzoxazoles leti fambelanaka (4af, 4ag na 4ai-4an) eka mbuyelo lowu enerisaka. Ti aldehydes letingana mintlawa yo humesa ti electron (xikombiso -CN na NO2) na tona ti endlile kahle naswona tinyika switirhisiwa leswi lavekaka (4ah na 4ao) eka mbuyelo wale henhla.
Nxaxamelo wa swiendlo leswi tirhisiwaka eka ku endliwa ka ti aldehydes a na b. a Swiyimo swa nhlamulo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mol%) swi endliwile eka EtOH (3 mL) eka 60 °C kuringana 6 h. b Mbuyelo wu fambelana na xiendliwa lexi hambanisiweke.
Ti polycyclic aromatic aldehydes tofana na 1-naphthaldehyde, anthracene-9-carboxaldehyde na phenanthrene-9-carboxaldehyde tinga humesa switirhisiwa leswi lavekaka 4ap-4ar eka mbuyelo wale henhla. Ti heterocyclic aromatic aldehydes tohambana hambana kukatsa na pyrrole, indole, pyridine, furan na thiophene ti tiyisela swiyimo swa reaction kahle naswona tinga humesa switirhisiwa leswi fambelanaka (4as-4az) eka mbuyelo wale henhla. Benzoxazole 4aag yikumeke eka 52% wa mbuyelo hiku tirhisa aliphatic aldehyde leyi fambelanaka.
Ndzhawu ya nhlamulo hiku tirhisa ti aldehydes ta mabindzu a, b. a Swiyimo swa nhlamulo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mol %) swi endliwile eka EtOH (5 mL) eka 60 °C kuringana 4 h. b Mbuyelo wu fambelana na xiendliwa lexi hambanisiweke. c Ku cinca cinca ku endliwile eka 80 °C kuringana 6 h; d Ku cinca cinca ku endliwile eka 100 °C kuringana 24 h.
Ku ya emahlweni hi kombisa ku cinca-cinca ni ku tirhisiwa ka ndlela leyi, hi tlhele hi kambela ti- catechol to hambana-hambana leti nga siviwa. Ti catechols letinga siviwa hi monosubstituted tofana na 4-tert-butylbenzene-1,2-diol na 3-methoxybenzene-1,2-diol ti endlile kahle na protocol leyi, leswinga nyika ti benzoxazoles 4aaa–4aac eka 89%, 86%, na 57% wa mbuyelo, hiku landzelelana. Ti polysubstituted benzoxazoles tin’wana titlhele ti endliwa hiku humelela hiku tirhisa ti polysubstituted catechols leti fambelanaka (4aad–4aaf). Ku hava swikumiwa leswi kumiweke loko ku tirhisiwa ti catechols leti cinciweke leti pfumalaka ti electron to fana na 4-nitrobenzene-1,2-diol na 3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
Ku endliwa ka benzoxazole hi nhlayo ya gram swi endliwile hiku humelela ehansi ka swiyimo leswi antswisiweke, naswona compound 4f yi endliwile eka 85% wa mbuyelo lowu hambanisiweke (Figure 5).
Ku hlanganisiwa ka xikalo xa gram ka benzoxazole 4f. Swiyimo swa nhlamulo: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) na ZrCl4 (5 mol%) swi endliwile eka EtOH (25 mL) eka 60 °C kuringana 4 h.
Hiku ya hi datha ya matsalwa, endlelo ro angula leri ringaneleke ri ringanyetiwile eka ku endliwa ka ti benzoxazoles kusuka eka catechol, aldehyde, na ammonium acetate eka vukona bya ZrCl4 catalyst (Xifaniso 6). Catechol yinga chelate zirconium hiku hlanganisa mintlawa yimbirhi ya hydroxyl kuva yi endla core yosungula ya catalytic cycle (I)51. Eka xiyimo lexi, xiphemu xa semiquinone (II) xinga vumbiwa hiku tirhisa enol-keto tautomerization eka complex I58. Ntlawa wa carbonyl lowu vumbiweke eka intermediate (II) swi tikomba wu endla reaction na ammonium acetate ku vumba intermediate imine (III) 47. Xin’wana lexi nga kotekaka hileswaku imine (III^), leyi vumbiweke hi ku cinca ka aldehyde na ammonium acetate, yi endla reaction na ntlawa wa carbonyl ku vumba intermediate imine-phenol (IV) 59,60. Endzhaku ka sweswo, xiphemu xa le xikarhi (V) xi nga hundza eka intramolecular cyclization40. Eku heteleleni, V ya le xikarhi yi oxidized hi oxygen ya le xibakabakeni, yi humesa xiendliwa lexi lavekaka 4 naswona yi humesa zirconium complex ku sungula xirhendzevutani lexi landzelaka61,62.
Ti reagents hinkwato nati solvents ti xaviwile kusuka eka swihlovo swa mabindzu. Switirhisiwa hinkwaswo leswi tivekaka swi tiveka hiku pimanisiwa na spectral data na melting points ya tisampulu leti kamberiweke. Ti spectra ta 1H NMR (400 MHz) na 13C NMR (100 MHz) ti rhekhodiwile eka xitirhisiwa xa Brucker Avance DRX. Tindhawu to n’oka ti kumiwile eka xitirhisiwa xa Büchi B-545 eka capillary leyi pfulekeke. Ti reactions hinkwato ti langutisiwile hi thin-layer chromatography (TLC) hiku tirhisa ti silica gel plates (Silica gel 60 F254, Merck Chemical Company). Nxopaxopo wa elemente wu endliwile eka PerkinElmer 240-B Microanalyzer.
Nkatsakanyo wa catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) na ZrCl4 (5 mol %) eka ethanol (3.0 mL) wu hlanganisiwile hiku landzelelana eka chubu leri pfulekeke eka bath ya oyili eka 60 °C ehansi ka moya kuringana nkarhi lowu lavekaka. Kuya emahlweni ka reaction swilangutiwile hi thin layer chromatography (TLC). Endzhaku ko hetisa reaction, nkatsakanyo lowu humelelaka wu titimerile kuya eka mahiselo ya kamara naswona ethanol yi susiwile ehansi ka ntshikelelo lowu hungutiweke. Nkatsakanyo wa reaction wu cheriwile hi EtOAc (3 x 5 mL). Kutani, ti organic layers leti hlanganisiweke ti omisiwa eka anhydrous Na2SO4 kutani ti hlanganisiwa eka vacuum. Eku heteleleni, nkatsakanyo lowu nga si swekiwaka wu basisiwile hi column chromatography hiku tirhisa petroleum ether/EtOAc tani hi eluent kuva ku nyikiwa benzoxazole yo basa 4.
Hiku komisa, hi tumbuluxile protocol ya novhele, yo olova na ya rihlaza ya ku endliwa ka ti benzoxazoles hiku tirhisa ku tumbuluxiwa hiku landzelelana ka CN na CO bonds eka vukona bya zirconium catalyst. Ehansi ka swiyimo swa nhlamulo leswi antswisiweke, 59 wa ti benzoxazoles to hambana ti endliwile. Swiyimo swa reaction swi fambisana na mintlawa yohambana hambana ya ntirho, naswona ti bioactive cores to hlaya ti endliwile hiku humelela, leswi kombaka vuswikoti bya tona byale henhla eka ntirho lowu landzelaka. Hikokwalaho, hi tumbuluxile maqhinga lawa ya tirhaka kahle, yo olova no tirha ya vuhumelerisi bya xikalo lexikulu xa switirhisiwa swohambana hambana swa benzoxazole kusuka eka ti catechols ta ntumbuluko ehansi ka swiyimo swa rihlaza hiku tirhisa ti catalysts ta ntsengo wale hansi.
Data hinkwayo leyi kumiweke kumbe ku xopaxopiwa hi nkarhi wa ndzavisiso lowu yi katsiwile eka atikili leyi leyi kandziyisiweke na tifayela ta yona ta Mahungu yo Engetela.
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