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Kafukufukuyu akufotokoza njira yothandiza kwambiri yopangira benzoxazoles pogwiritsa ntchito catechol, aldehyde ndi ammonium acetate ngati chakudya kudzera mu coupling reaction mu ethanol ndi ZrCl4 ngati catalyst. Mndandanda wa benzoxazoles (mitundu 59) unapangidwa bwino ndi njira iyi mu zokolola zofika 97%. Ubwino wina wa njira iyi ndi kuphatikiza kwakukulu ndi kugwiritsa ntchito mpweya ngati oxidizing agent. Mikhalidwe yofatsa ya reaction imalola kugwira ntchito pambuyo pake, komwe kumathandizira kupanga zinthu zosiyanasiyana zomwe zili ndi kapangidwe kogwirizana ndi zamoyo monga β-lactams ndi quinoline heterocycles.
Kupanga njira zatsopano zopangira zinthu zachilengedwe zomwe zingathe kuthana ndi zolepheretsa kupeza mankhwala amtengo wapatali ndikuwonjezera kusiyanasiyana kwawo (kuti atsegule madera atsopano ogwiritsira ntchito) kwakopa chidwi chachikulu m'masukulu ndi m'mafakitale1,2. Kuphatikiza pa kugwira ntchito bwino kwa njirazi, kusamala chilengedwe kwa njira zomwe zikupangidwa kudzakhalanso phindu lalikulu3,4.
Benzoxazoles ndi gulu la mankhwala opangidwa ndi heterocyclic omwe akope chidwi chachikulu chifukwa cha ntchito zawo zambiri zamoyo. Mankhwala oterewa akuti ali ndi maantibayotiki, oteteza mitsempha, oletsa khansa, oletsa mavairasi, oletsa mabakiteriya, oletsa bowa, komanso oletsa kutupa5,6,7,8,9,10,11. Amagwiritsidwanso ntchito kwambiri m'mafakitale osiyanasiyana kuphatikiza mankhwala, masensa, agrochemistry, ligands (yothandizira kusintha kwa metal catalysis), ndi sayansi ya zinthu12,13,14,15,16,17. Chifukwa cha mphamvu zawo zapadera zamakemikolo komanso kusinthasintha kwawo, benzoxazoles akhala zinthu zofunika kwambiri popanga mamolekyu ambiri ovuta a organic18,19,20. Chosangalatsa n'chakuti, ma benzoxazoles ena ndi zinthu zachilengedwe zofunika komanso mamolekyu ofunikira pamankhwala, monga nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 ndi neosalvianene (Chithunzi 1A)26.
(A) Zitsanzo za zinthu zachilengedwe zochokera ku benzoxazole ndi mankhwala ophatikizika ndi zinthu zachilengedwe. (B) Magwero ena achilengedwe a ma catechol.
Ma Catechol amagwiritsidwa ntchito kwambiri m'magawo ambiri monga mankhwala, zodzoladzola ndi sayansi ya zinthu27,28,29,30,31. Ma Catechol awonetsedwanso kuti ali ndi mphamvu zotsutsana ndi kutupa komanso zotsutsana ndi kutupa, zomwe zimapangitsa kuti akhale othandizira kuchiritsa32,33. Katunduyu wapangitsa kuti agwiritsidwe ntchito popanga zodzoladzola zotsutsana ndi ukalamba ndi zinthu zosamalira khungu34,35,36. Kuphatikiza apo, ma Catechol awonetsedwa kuti ndi oyambitsa bwino kupanga zinthu zachilengedwe (Chithunzi 1B)37,38. Ena mwa ma Catechol awa ndi ambiri mwachilengedwe. Chifukwa chake, kugwiritsidwa ntchito kwake ngati zinthu zopangira kapena zinthu zoyambira kupanga zinthu zachilengedwe kumatha kukhala ndi mfundo yobiriwira ya "kugwiritsa ntchito zinthu zongowonjezwdwa". Njira zingapo zosiyanasiyana zapangidwa kuti zikonzekeretse mankhwala a benzoxazole ogwiritsidwa ntchito7,39. Kugwira ntchito kwa okosijeni kwa mgwirizano wa C(aryl)-OH wa ma Catechol ndi njira imodzi yosangalatsa komanso yatsopano yopangira ma benzoxazoles. Zitsanzo za njira iyi popanga benzoxazoles ndi momwe ma catechol ndi ma amines40,41,42,43,44 amachitira, ndi aldehydes45,46,47, ndi ma alcohols (kapena ethers)48, komanso ndi ma ketones, alkenes ndi ma alkynes (Chithunzi 2A)49. Mu kafukufukuyu, multicomponent reaction (MCR) pakati pa catechol, aldehyde ndi ammonium acetate idagwiritsidwa ntchito popanga benzoxazoles (Chithunzi 2B). Zomwe zimachitikazi zidachitika pogwiritsa ntchito kuchuluka kwa catalytic kwa ZrCl4 mu ethanol solvent. Dziwani kuti ZrCl4 ikhoza kuonedwa ngati green Lewis acid catalyst, ndi compound yopanda poizoni [LD50 (ZrCl4, pakamwa pa makoswe) = 1688 mg kg−1] ndipo siionedwa kuti ndi yoopsa kwambiri50. Zirconium catalysts zagwiritsidwanso ntchito bwino ngati catalysts popanga mankhwala osiyanasiyana achilengedwe. Mtengo wawo wotsika komanso kukhazikika kwawo kwakukulu ku madzi ndi mpweya zimapangitsa kuti zikhale zolimbikitsa kwambiri mu kapangidwe ka organic51.
Kuti tipeze momwe zinthu zilili zoyenera, tinasankha 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a ndi ammonium salt 3 ngati chitsanzo cha machitidwe ndipo tinachita machitidwewo pamaso pa ma Lewis acids osiyanasiyana (LA), ma solvents osiyanasiyana ndi kutentha kuti tipange benzoxazole 4a (Table 1). Palibe chinthu chomwe chinawonedwa popanda catalyst (Table 1, gawo 1). Pambuyo pake, 5 mol % ya ma Lewis acids osiyanasiyana monga ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 ndi MoO3 adayesedwa ngati ma catalyst mu EtOH solvent ndipo ZrCl4 idapezeka kuti ndi yabwino kwambiri (Table 1, zolemba 2–8). Kuti zinthu ziyende bwino, zinthu zosiyanasiyana zosungunulira zinayesedwa kuphatikizapo dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) ndi dimethyl sulfoxide (DMSO). Zokolola za zinthu zonse zosungunulira zomwe zinayesedwa zinali zochepa kuposa za ethanol (Table 1, zolemba 9-15). Kugwiritsa ntchito magwero ena a nayitrogeni (monga NH4Cl, NH4CN ndi (NH4)2SO4) m'malo mwa ammonium acetate sikunawongolere zokolola za reaction (Table 1, zolemba 16-18). Kafukufuku wina anasonyeza kuti kutentha pansi pa 60 °C ndi pamwamba pa 60 °C sikunawongolere zokolola za reaction (Table 1, zolemba 19 ndi 20). Pamene catalyst loading inasinthidwa kukhala 2 ndi 10 mol %, zokolola zinali 78% ndi 92%, motsatana (Table 1, zolemba 21 ndi 22). Kuchuluka kwa zokolola kunachepa pamene kuchitidwa kwa zinthuzo kunachitidwa pansi pa mlengalenga wa nayitrogeni, zomwe zikusonyeza kuti mpweya wa mumlengalenga ukhoza kukhala ndi gawo lofunika kwambiri pa kuchitidwa kwa zinthuzo (Table 1, gawo 23). Kuwonjezeka kwa kuchuluka kwa ammonium acetate sikunawongolere zotsatira za kuchitidwa kwa zinthuzo komanso kunachepetsanso kuchuluka kwa zokolola (Table 1, magawo 24 ndi 25). Kuphatikiza apo, palibe kusintha kwa kuchuluka kwa zokolola zomwe zinawonedwa powonjezera kuchuluka kwa catechol (Table 1, gawo 26).
Pambuyo podziwa momwe zinthu zilili bwino, kusinthasintha ndi kugwiritsa ntchito kwa zomwe zimachitikazo kunaphunziridwa (Chithunzi 3). Popeza ma alkynes ndi ma alkenes ali ndi magulu ofunikira pantchito yopanga zinthu zachilengedwe ndipo amatha kusinthidwa mosavuta, zinthu zingapo zochokera ku benzoxazole zinapangidwa ndi ma alkenes ndi ma alkynes (4b–4d, 4f–4g). Pogwiritsa ntchito 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde ngati gawo la aldehyde (4e), zokolola zinafika 90%. Kuphatikiza apo, ma benzoxazoles osinthidwa ndi alkyl halo adapangidwa mu zokolola zambiri, zomwe zingagwiritsidwe ntchito polumikizana ndi mamolekyu ena ndi zokolola zina (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde ndi 4-(benzyloxy)benzaldehyde adapereka benzoxazoles 4j ndi 4k mu zokolola zambiri, motsatana. Pogwiritsa ntchito njira iyi, tinapanga bwino zinthu zochokera ku benzoxazole (4l ndi 4m) zokhala ndi quinolone moieties53,54,55. Benzoxazole 4n yokhala ndi magulu awiri a alkyne idapangidwa ndi 84% kuchokera ku benzaldehydes 2,4-substituted. Bicyclic compound 4o yokhala ndi indole heterocycle idapangidwa bwino pansi pa mikhalidwe yabwino. Compound 4p idapangidwa pogwiritsa ntchito aldehyde substrate yolumikizidwa ku gulu la benzonitrile, lomwe ndi substrate yothandiza pokonzekera ma (4q-4r) supramolecules56. Kuti tiwonetse momwe njira iyi ikugwiritsidwira ntchito, kukonzekera mamolekyulu a benzoxazole okhala ndi β-lactam moieties (4q-4r) kudawonetsedwa pansi pa mikhalidwe yabwino kudzera mu reaction ya aldehyde-functionalized β-lactams, catechol, ndi ammonium acetate. Kuyesera kumeneku kukuwonetsa kuti njira yatsopano yopangira ingagwiritsidwe ntchito pochita ntchito mochedwa mamolekyu ovuta.
Kuti tipitirize kusonyeza kusinthasintha ndi kulekerera kwa njira iyi ku magulu ogwira ntchito, tinaphunzira mitundu yosiyanasiyana ya aldehydes aromatic kuphatikizapo magulu opereka ma electron, magulu ochotsa ma electron, mankhwala a heterocyclic, ndi ma polycyclic aromatic hydrocarbons (Chithunzi 4, 4s–4aag). Mwachitsanzo, benzaldehyde inasinthidwa kukhala chinthu chomwe chikufunika (4s) mu 92% yokolola yokha. Ma aldehydes aromatic okhala ndi magulu opereka ma electron (kuphatikiza -Me, isopropyl, tert-butyl, hydroxyl, ndi para-SMe) adasinthidwa bwino kukhala zinthu zomwe zikugwirizana mu zokolola zabwino kwambiri (4t–4x). Ma substrates a aldehyde oletsedwa bwino amatha kupanga zinthu za benzoxazole (4y–4aa, 4al) mu zokolola zabwino mpaka zabwino kwambiri. Kugwiritsa ntchito meta-substituted benzaldehydes (4ab, 4ai, 4am) kunalola kukonzekera zinthu za benzoxazole mu zokolola zambiri. Ma aldehydes okhala ndi halogenated monga (-F, -CF3, -Cl ndi Br) adapereka ma benzoxazoles ofanana (4af, 4ag ndi 4ai-4an) mu zokolola zokwanira. Ma Aldehydes okhala ndi magulu ochotsa ma electron (monga -CN ndi NO2) nawonso adachita bwino ndipo adapereka zinthu zomwe amafunikira (4ah ndi 4ao) mu zokolola zambiri.
Mndandanda wa zochita zomwe zimagwiritsidwa ntchito popanga aldehydes a ndi b. a Mikhalidwe ya zochita: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) ndi ZrCl4 (5 mol%) zinayankhidwa mu EtOH (3 mL) pa 60 °C kwa maola 6. b Zokololazo zikugwirizana ndi zomwe zapezeka.
Ma polycyclic aromatic aldehydes monga 1-naphthaldehyde, anthracene-9-carboxaldehyde ndi phenanthrene-9-carboxaldehyde angapangitse zinthu zomwe zimafunidwa kukhala 4ap-4ar mu zokolola zambiri. Ma heterocyclic aromatic aldehydes osiyanasiyana kuphatikizapo pyrrole, indole, pyridine, furan ndi thiophene adapirira bwino momwe zinthu zimachitikira ndipo amatha kupanga zinthu zomwe zikugwirizana (4as-4az) mu zokolola zambiri. Benzoxazole 4aag idapezeka mu zokolola za 52% pogwiritsa ntchito aliphatic aldehyde yofanana.
Chigawo cha reaction pogwiritsa ntchito aldehydes zamalonda a, b. a Mikhalidwe ya reaction: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) ndi ZrCl4 (5 mol %) zinayankhidwa mu EtOH (5 mL) pa 60 °C kwa maola 4. b Zokololazo zikugwirizana ndi zomwe zapezeka. c Yankho linachitika pa 80 °C kwa maola 6; d Yankho linachitika pa 100 °C kwa maola 24.
Kuti tipitirize kusonyeza kusinthasintha ndi kugwiritsidwa ntchito kwa njira iyi, tinayesanso ma catechol osiyanasiyana osinthidwa. Ma catechol osinthidwa motsatizana monga 4-tert-butylbenzene-1,2-diol ndi 3-methoxybenzene-1,2-diol adagwira ntchito bwino ndi njira iyi, zomwe zidapangitsa kuti benzoxazoles 4aaa–4aac ikhale ndi zokolola 89%, 86%, ndi 57% motsatana. Ma benzoxazoles ena osinthidwa motsatizana adapangidwanso bwino pogwiritsa ntchito ma catechol osinthidwa motsatizana (4aad–4aaf). Palibe zinthu zomwe zidapezeka pamene ma catechol osinthidwa opanda ma elekitironi monga 4-nitrobenzene-1,2-diol ndi 3,4,5,6-tetrabromobenzene-1,2-diol adagwiritsidwa ntchito (4aah–4aai).
Kupanga kwa benzoxazole mu magalamu ambiri kunatheka bwino pansi pa mikhalidwe yabwino, ndipo compound 4f inapangidwa mu 85% yochokera mu chigawo chimodzi (Chithunzi 5).
Kupanga kwa benzoxazole 4f pogwiritsa ntchito sikelo ya gramu. Mikhalidwe ya reaction: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) ndi ZrCl4 (5 mol%) zinayankhidwa mu EtOH (25 mL) pa 60 °C kwa maola 4.
Kutengera ndi deta ya mabuku, njira yolondola yochitira zinthu yaperekedwa kuti ipange benzoxazoles kuchokera ku catechol, aldehyde, ndi ammonium acetate pamaso pa ZrCl4 catalyst (Chithunzi 6). Catechol imatha kupanga zirconium mwa kugwirizanitsa magulu awiri a hydroxyl kuti apange core yoyamba ya catalytic cycle (I)51. Pankhaniyi, semiquinone moiety (II) ikhoza kupangidwa kudzera mu enol-keto tautomerization mu complex I58. Gulu la carbonyl lopangidwa mu intermediate (II) mwachiwonekere limakumana ndi ammonium acetate kuti lipange intermediate imine (III) 47. Kuthekera kwina ndikuti imine (III^), yopangidwa ndi aldehyde ndi ammonium acetate, imakumana ndi gulu la carbonyl kuti ipange intermediate imine-phenol (IV) 59,60. Pambuyo pake, intermediate (V) imatha kupitilira intramolecular cyclization40. Pomaliza, pakati pa V imasungunuka ndi mpweya wa mumlengalenga, zomwe zimapangitsa kuti chinthu chomwe chikufunidwa chikhalepo 4 ndikutulutsa zirconium complex kuti iyambe kuzungulira kwina61,62.
Ma reagents ndi zosungunulira zonse zinagulidwa kuchokera kuzinthu zamalonda. Zinthu zonse zodziwika zinapezeka poyerekeza ndi deta ya spectral ndi malo osungunuka a zitsanzo zoyesedwa. Ma spectra a 1H NMR (400 MHz) ndi 13C NMR (100 MHz) adalembedwa pa chida cha Brucker Avance DRX. Malo osungunuka adapezeka pa chipangizo cha Büchi B-545 mu capillary yotseguka. Machitidwe onse adayang'aniridwa ndi thin-layer chromatography (TLC) pogwiritsa ntchito mbale za silica gel (Silica gel 60 F254, Merck Chemical Company). Kusanthula kwa elemental kunachitika pa PerkinElmer 240-B Microanalyzer.
Yankho la catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) ndi ZrCl4 (5 mol %) mu ethanol (3.0 mL) linasunthidwa motsatizana mu chubu chotseguka mu bafa la mafuta pa 60 °C pansi pa mpweya kwa nthawi yofunikira. Kupita patsogolo kwa reaction kunayang'aniridwa ndi thin layer chromatography (TLC). Pambuyo pomaliza reaction, osakaniza omwe adatuluka adazizidwa kutentha kwa chipinda ndipo ethanol idachotsedwa pansi pa kupsinjika kochepa. Osakaniza reaction adachepetsedwa ndi EtOAc (3 x 5 mL). Kenako, zigawo zophatikizika za organic zidaumitsidwa pa anhydrous Na2SO4 ndikuyikidwa mu vacuo. Pomaliza, osakaniza osaphikidwa adayeretsedwa ndi column chromatography pogwiritsa ntchito petroleum ether/EtOAc ngati njira yabwino yopezera benzoxazole 4 yoyera.
Mwachidule, tapanga njira yatsopano, yofatsa komanso yobiriwira yopangira ma benzoxazoles kudzera mu kapangidwe kotsatizana ka ma CN ndi ma CO bond pamaso pa zirconium catalyst. Pansi pa mikhalidwe yabwino kwambiri yochitira, ma benzoxazoles 59 osiyanasiyana adapangidwa. Mikhalidwe ya reaction imagwirizana ndi magulu osiyanasiyana ogwira ntchito, ndipo ma cores angapo ogwira ntchito m'thupi adapangidwa bwino, zomwe zikusonyeza kuthekera kwawo kwakukulu kogwirira ntchito pambuyo pake. Chifukwa chake, tapanga njira yothandiza, yosavuta komanso yothandiza yopangira zinthu zosiyanasiyana zochokera ku benzoxazole kuchokera ku ma catechol achilengedwe pansi pa mikhalidwe yobiriwira pogwiritsa ntchito ma catalyst otsika mtengo.
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