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Okucondooza oku nikuha orupapura rw’omuringo gw’okukora gye munonga ogw’okukora ebirungo bya benzoxazoles barikukoresa catechol, aldehyde na ammonium acetate nk’eby’okurya kurabira omu kuteerana omu ethanol na ZrCl4 nk’ekirikureetaho. Omubaro gwa benzoxazoles (ebika 59) gukabaasa kukorwa omu muringo ogu omu bihingwa ebirikuhika ahari 97%. Ebindi birungi ebiri omu nkora egi harimu okukora ebintu bingi n’okukoresa oxygen nk’ekintu ekirikureetaho okwitsya. Embeera z‘okugarukamu ezitari nkuru niziikiriza okukora okurikukuratiraho, ekirikuhwera omu kuteerana kw‘ebintu ebitari bimwe na bimwe ebirikuruga omu bihangirwe ebiine akakwate n‘ebihangirwe nka β-lactams na quinoline heterocycles.
Okukora emiringo mirungi y’okukora ebintu ebiine amagara ebirikubaasa kusingura oburemeezi omu kutunga ebirungo by’omuhendo gw’ahaiguru n’okwongyera aha nkora yaabyo (kwiguraho emyanya mirungi y’okukoresa) kireetaire abantu baingi kuteekateeka munonga omu by’obwegyese n’omu by’amakorero1,2. Okwongyera aha burungi bw‘ahaiguru bw‘emiringo egi, okurinda eby‘obuhangwa kw‘enkora ezirikukorwa nakwo nikwija kuba omugasho gw‘amaani3,4.
Benzoxazoles n’ekibiina ky’ebintu ebitarikushushana ebitungire omutima gw’abantu baingi ahabw’emirimo yaabyo mingi ey’ebihangirwe. Ebirungo nk’ebi bigambirweho kuba biine emirimo y’okurwanisa obukooko oburikureeta endwara, okurinda obutafaari bw’omubiri, okurwanisa ekookoro, okurwanisa obukooko oburikureeta endwara, okurwanisa obukooko oburikureeta endwara, okurwanisa obukooko oburikureeta endwara, n’okurwanisa okuzimba5,6,7,8,9,10,11. Kandi nizikoresibwa munonga omu mirimo y’amakorero etari emwe n’emwe otwariremu eby’emibazi, eby’okuhurira, eby’obuhingi n’oburiisa, eby’okuteerana (eby’okuhindura eby’ekyoma), n’eby’okukoresa12,13,14,15,16,17. Ahabw’emitwarize yaabo ey’omutaano ey’eby’obuhangwa n’okubaasa kukora ebintu bingi, benzoxazoles zihindukire ebintu bikuru eby’okwombeka eby’obuhangwa bingi ebigumire18,19,20. Ekirikushemeza, ebimwe aha bihingwa ebirikwetwa benzoxazoles n’ebintu bikuru eby’obuhangwa kandi n’ebicweka by’omubiri ebiine akakwate n’eby’emibazi, nka nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 na neosalvianene (ekishushani 1A)26.
(A) Eby‘okureeberaho by‘ebintu by‘obuhangwa ebirikwegamira ahari benzoxazole n‘ebirungo by‘amagara. (B) Ebimwe aha bintu by’obuhangwa ebirikuruga omu katekoli.
Katekoli nizikoresibwa munonga omu miringo mingi nk’eby’emibazi, eby’okujwara n’eby’okukoresa27,28,29,30,31. Catechols nazo zikworekwa ngu ziine ebirikurwanisa obukooko oburikureeta endwara n‘okurwanisa okuzimba, ekirikuzihindura ezirikubaasa kukoresibwa nk‘ebintu by‘okujanjaba32,33. Ekintu eki kireetsireho okukikozesa omu kuhanga eby‘okujwara ebirikurwanisa okukura n‘ebintu by‘okureeberera oruhu34,35,36. Ekindi, katekoli zikworekwa kuba nizikora gye omu kutandika kw’ebintu ebiine amagara (ekishushani 1B)37,38. Ebimwe ahari ebi katekoli nibikanyira kimwe omu buhangwa. Nahabwekyo, okugikozesa nk’ekintu ekikuru nari ekirikutandikiraho okukora eby’obuhangwa nikibaasa kujwanzya omusingye gwa green chemistry ogwa “okukozesa eby’obugaiga ebirikugarukaho”. Emihanda mingi etari emwe n‘emwe ekozirwe kutebeekanisa ebirungo bya benzoxazole ebirikukora7,39. Okukora kwa oksijeni kw’omukago gwa C(aryl)-OH gwa katekoli n’emwe aha miringo erikushemeza kandi ensya ey’okukora benzoxazoles. Eby’okureeberaho by’enkora egi omu kuhangaho ebiriisa bya benzoxazoles n’okugarukamu kwa katekoli n’amine40,41,42,43,44, n’ebiriisa bya aldehydes45,46,47, n’eby’okunywa (nari shi ethers)48, hamwe n’eby’okurya bya ketoni, alkenes na alkinas (Ekishushani 2A)49. Omu kucondooza oku, okugarukamu kw’ebicweka bingi (MCR) ahagati ya katekoli, aldehyde na ammonium asetate kukakoresibwa omu kuhangaho benzoxazoles (ekishushani 2B). Okugarukamu oku kukakorwa barikukoresa omubaro gw’ekiriisa kya ZrCl4 omu kirungo kya ethanol. Yetegyereze ngu ZrCl4 neebaasa kuteekateekwaho nk‘ekirikureetaho asidi ya Lewis eya kinyasi, n‘ekirungo ky‘obutwa bukye [LD50 (ZrCl4, omu kanwa ahabw‘enkyenzi) = 1688 mg kg−1] kandi tikirikuteekateekwaho kuba eky‘obutwa bwingi50. Zirconium catalysts nazo zikoresiibwe gye nk’ebikwato by’okukora ebintu bitari bimwe na bimwe ebiine amagara. Omuhendo gwazo mukye n’okugumaho kw’ahaiguru aha maizi n’omwika gw’omwika nibizireetera kuba eby’okureeberaho by’okukora eby’obuhangwa51.
Kubaasa kutunga embeera z‘okugarukamu ezihikire, tukatoorana 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a n‘omunyugunyu gwa ammonium 3 nk‘okugarukamu kw‘eky‘okureeberaho kandi twakora okugarukamu omu kubaho kwa asidi za Lewis zitari zimwe na zimwe (LA), ebirungo bya synthezo ebitarikushushana n‘obutagatsi1). Tihariho kintu ekyareebirwe omu kubura kw‘ekirikureetaho (Ekipande 1, enyuguta 1). Okurugirira ahari ekyo, 5 mol % ya asidi za Lewis zitari zimwe na zimwe nka ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 na MoO3 zikakyeberwa nk’ebirikureetaho okuhinduka kw’ebintu omu nkora ya EtOH kandi ZrCl4 ekashangwa eri nungi, Ent2–Tries). Okubaasa kutunguura okukora gye, ebirungo bitari bimwe na bimwe bikagyezibwa otwariremu dioxane, asetonitrile, ethyl asetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) na dimethyl sulfoxide (DMSO). Ebirugire omu bihingwa byona ebyagyeziibwe bikaba biri ahansi y’eby’okurya bya ethanol (Ekipande 1, ebihandiiko 9–15). Okukozesa ebindi bihingwa ebirimu nitrogen (nka NH4Cl, NH4CN na (NH4)2SO4) omu mwanya gw’okukoresa ammonium asetate tikukatunguura aha nkora y’okugarukamu (Ekipande 1, ebihandiiko 16–18). Okucondooza okundi kukooreka ngu ebirikuba biri ahansi n’ahaiguru ya 60 °C tibirikwongyera aha nkora y’okugarukamu (Ekipande 1, enyuguta 19 na 20). Okuremeera kw’ekiriisa kya catalyst ku kwahinduirwe kwaba 2 na 10 mol %, ebirikurugamu bikaba biri 78% na 92%, nk’oku biri (Ekipande 1, enyuguta 21 na 22). Okuhinga kukakyeera obu okugarukamu kwakorwa ahansi y’omuyaga gwa nitrogen, ekirikworeka ngu oxygen y’omu mwanya neebaasa kukora omurimo muhango omu kugarukamu (Ekipande 1, enyuguta 23). Okwongyera aha mubaro gwa ammonium acetate tikwatunguura ebyarugamu omu kugarukamu kandi nangwa n’okukyendeeza aha ntunguuka (Ekipande 1, enyuguta 24 na 25). Okwongyera ahari ekyo, tihaine kutunguuka omu kureetaho okugarukamu okwareebirwe n‘okwongyera aha mubaro gwa katekoli (Ekipande 1, enyuguta 26).
Bwanyima y‘okumanyisa embeera z‘okugarukamu ezihikire, okuhindura n‘okukoresa kw‘okugarukamu kukakyeberwa (ekishushani 3). Ahabw’okugira ngu alkynes na alkenes ziine guruupu z’emirimo z’omugasho omu kuhanga ebintu kandi nizibaasa kworoba kwongyera kuhindurwa, ebirugire omu benzoxazole bingi bikakorwa na alkenes na alkynes (4b–4d, 4f–4g). Okukozesa 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde nk’omubazi gw’okukyebera (4e), ebirikurugamu bikahika ahari 90%. Okwongyera ahari ekyo, ebiriisa bya alkyl halo-substituted benzoxazoles bikakorwa omu nkora y’okutunga ebiriisa bingi, ebirikubaasa kukoresibwa omu kukwatira hamwe n’ebindi bihingwa n’okwongyera aha kureetaho ebiriisa (4h–4i) 52. omu bihingwa bingi, nk’oku biri. Okukozesa omuringo ogu, tukabaasa kushoboorora gye ebirugire omu benzoxazole (4l na 4m) ebirimu ebicweka bya quinolone53,54,55. Benzoxazole 4n erimu guruupu ibiri za alkyne ekakorwa omu 84% kuruga omu 2,4-ebiri omu mwanya gwa benzaldehydes. Ekirungo ky’obugaari 4o ekirimu indole heterocycle kikabaasa kukorwa omu mbeera nungi. Ekirungo 4p kikakorwa barikukoresa ekirungo kya aldehyde ekikwatsire aha guruupu ya benzonitrile, ekirungo ky’omugasho omu kutebeekanisa (4q-4r) supramolecules56. Okushoboorora oku omuringo ogu gurikubaasa kukoresibwa, okutebeekanisa ebicweka bya benzoxazole ebirimu ebicweka bya β-lactam (4q–4r) kukareebeka omu mbeera ezihikire kurabira omu kugarukamu kwa β-lactams ezirikukoresibwa aldehyde, catechol, na ammonium acetate. Okucondooza oku nikworeka ngu enkora ensya ey’okukora eby’obuhangwa neebaasa kukoresibwa omu kukora kw’ebicweka by’omubiri ebigumire omu bwire bw’enyima.
Okwongyera kworeka obukomooko n‘okugumisiriza kw‘omuringo ogu aha guruupu z‘emirimo, tukacondooza aha aldehydes z‘omubazi zitari zimwe na zimwe ezirimu guruupu ezirikuha amashanyarazi, guruupu ezirikuiha amashanyarazi, ebirungo by‘ebicweka by‘omubiri ebitarikushushana, n‘ebicweka by‘omubiri ebiine amaizi g‘omubiri (Ekishushani 4, 4s–4aag). Nk’eky’okureeberaho, benzaldehyde ekahindurwa kuba ekintu ekirikwetengwa (4s) omu 92% y’okuhinga okutaine rubaju. Aldehydes z’omubazi eziine guruupu ezirikuha amashanyarazi (obariiremu -Me, isopropyl, tert-butyl, hydroxyl, na para-SMe) zikaba zihindurwa gye zikaba ebintu ebirikushushana omu bihingwa birungi munonga (4t–4x). Ebicweka bya aldehyde ebiine oburemeezi bw’okutambura nibibaasa kureetaho ebintu bya benzoxazole (4y–4aa, 4al) omu bihingwa birungi kuhika aha birungi munonga. Okukozesa ebiriisa ebiine ebiriisa bya meta (4ab, 4ai, 4am) kikabaasisa okutebeekanisa ebintu bya benzoxazole omu bihingwa bingi. Aldehydes ezirimu halojeni nka (-F, -CF3, -Cl na Br) zikaha ebiriisa ebirikuhikaana (4af, 4ag na 4ai-4an) omu bihingwa ebirikumara. Aldehydes eziine guruupu z’okuihaho electron (nk’eky’okureeberaho -CN na NO2) nazo zikaba zikora gye kandi ziha ebirugiremu ebirikwetengyesa (4ah na 4ao) omu kutunga ebiriisa bingi.
Omubaro gw’okugarukamu ogurikukoresibwa omu kuteerana aldehydes a na b. a Embeera z’okugarukamu: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mmol%) bikagarukwamu omu EtOH (3 mL) ahari 60 °C kumara eshaaha 6 h. b Ebirikurugamu nibihikaana n’ekirugiremu ekitaanisiibweho.
Ebirungo by’omubiri ebirimu ebiriisa bingi nka 1-naphthaldehyde, anthracene-9-carboxaldehyde na phenanthrene-9-carboxaldehyde nibibaasa kureetaho ebintu ebirikwetengyesa 4ap-4ar omu kuhinga kwingi. Ebirungo by’omubiri ebitari bimwe na bimwe ebirimu pyrrole, indole, pyridine, furan na thiophene bikagumisiriza gye embeera z’okugarukamu kandi bikabaasa kureetaho ebintu ebirikuhikaana (4as-4az) omu bihingwa bingi. Benzoxazole 4aag ekatunga omu 52% y’okuhinga barikukoresa omubazi ogurikuhikaana n’ogwo.
Ekicweka ky’okugarukamu kirikukoresa aldehydes z’eby’obushuubuzi a, b. a Embeera z’okugarukamu: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mmol %) bikagarukwamu omu EtOH (5 mL) ahari 60 °C kumara eshaaha 4 h. b Ebirikurugamu nibihikaana n’ekirugiremu ekitaanisiibweho. c Okugarukamu kukakorwa aha 80 °C kumara eshaaha 6; d Okugarukamu kukakorwa aha 100 °C kumara 24 h.
Okwongyera kworeka oku omuringo ogu gurikubaasa kukoresibwa omu miringo mingi n’oku gurikubaasa kukoresibwa, tukagyezaho n’ebikwato bitari bimwe na bimwe ebirikuhindurwa katekoli. Ebihingwa ebiine ebiriisa bimwe nka 4-tert-butylbenzene-1,2-diol na 3-methoxybenzene-1,2-diol bikakwatagana gye n’omuringo ogu, byaha benzoxazoles 4aaa–4aac omu 89%, 86%, na 57% eby’okurya, nk’oku biri. Ebimwe aha bihingwa bya benzoxazoles ebiine ebiriisa bingi nabyo bikabaasa kukorwa gye barikukoresa catechols eziine ebiriisa bingi ebirikuhikaana (4aad–4aaf). Tihariho ebintu ebyatungirwe obu baakoresa katekoli eziine obuzibu bw’okuhindura ebiriisa nk’eby’okurya ebirimu ebiriisa nk’ebiriisa (4aah–4aai).
Okuteerana kwa benzoxazole omu bwingi bwa gram kukahikirizibwa gye omu mbeera ezihikire, kandi ekirungo 4f kikakorwa omu 85% y’eby’okurya ebitari bimwe na bimwe (ekishushani 5).
Okuteerana kw’eby’okurya ebirimu ebiriisa bya gram 4f. Embeera z’okugarukamu: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) na ZrCl4 (5 mol%) bikagarukwamu omu EtOH (25 mL) ahari 60 °C kumara eshaaha 4 h.
Okurugirira aha bihandiiko, omuringo gw‘okugarukamu oguhikire gukateebwaho ahabw‘okukora benzoxazoles kuruga omu catechol, aldehyde, na ammonium acetate omu kubaho kw‘ekirungo kya ZrCl4 (ekishushani 6). Catechol neebaasa kuhindura zirconium erikukoragana n’ebicweka bibiri bya hydroxyl kukora omusingi gw’okubanza ogw’omuringo gw’okuhindura (I)51. Omu muringo ogu, ekicweka kya semiquinone (II) nikibaasa kuhangwa kurabira omu kuhindura enol-keto omu nkora ya I58. Ekibiina kya kaboni ekihangirwe omu nkora y’ahagati (II) nikireebeka ngu nikikwatagana na ammonium asetate kuhanga imine y’ahagati (III) 47. Ekindi ekirikubaasa kubaho n’okugira ngu imine (III^), erikubaho ahabw’okukoragana kwa aldehyde na ammonium asetate, neekwatagana n’ekibiina kya kaboni kureetaho imine y’ahagati,IV60) . Okurugirira ahari ekyo, ebiri ahagati (V) nibibaasa kuraba omu nkora y’okuhinduka kw’omubiri40. Eky’aha muheru, V ey’ahagati neehindurwa oxygen n’omwika gw’omu mwanya, kireetaho ekirikwetengyesa 4 kandi kirekura zirconium complex kutandikaho omuzingo ogurikukurataho61,62.
Ebirikukoresibwa omu kukyebera n’okushohoza byona bikagurwa kuruga omu by’obushuubuzi. Ebintu byona ebyamanyirwe bikamanyirwa aha kugyeragyeranisa n’ebihandiiko bya spectral n’ebicweka by’okusheenya eby’okureeberaho ebyagyeziibwe. Ebishushani bya 1H NMR (400 MHz) na 13C NMR (100 MHz) bikahandiikwa aha kikwato kya Brucker Avance DRX. Ebicweka by’okusheenya bikamanyirwa aha kikwato kya Büchi B-545 omu nkora y’okusheenya erimu amaizi. Ebigarukwamu byona bikakyeberwa omu muringo gw’okukyebera ebiri omu nkora (TLC) barikukoresa ebipande bya silika gel (Silika gel 60 F254, Kampuni y’eby’emibazi eya Merck). Okushwijuma eby‘okureeberaho kukakorwa aha kikwato kya PerkinElmer 240-B eky‘okushwijuma.
Omubazi gwa katekoli (1.0 mmol), aldehaidi (1.0 mmol), ammoniyamu asetaiti (1.0 mmol) na ZrCl4 (5 mol %) omu ethanol (3.0 mL) gukakuratana omu ntuumo eigukire omu kyombeko ky’amajuta aha 60 °C ahansi y’omuyaga kumara obwire oburikwetengwa. Okutunguuka kw’okugarukamu kukakyeberwa omu muringo gw’okucondooza (TLC). Bwanyima y’okuheza kukora, omutaano ogwarugiremu gukakyendeezibwa kuhika aha butagasi bw’omu kishengye kandi ethanol ekaihwaho ahansi y’okukyendeeza aha nkora. Omutaano gw’okugarukamu gukakyeberwa na EtOAc (3 x 5 mL). Bwanyima, ebicweka by’ebihangwa ebiteeraine bikayomezibwa aha Na2SO4 etaine maizi kandi byateebwa omu mwanya ogutarimu kintu kyona. Eky’aha muheru, omutaano gw’ebishaju gukashemezibwa omu kukyebera kw’enyomyo barikukoresa ether/EtOAc nk’ekirungo ky’okutunga benzoxazole 4 eshemeire.
Omu bugufu, tukakora omuringo musya, ogw’obucureezi kandi ogw’ekibira ogw’okukora benzoxazoles kurabira omu kuhangaho okukuratana kw’enkoragana za CN na CO omu kubaho kwa zirconium catalyst. Omu mbeera z‘okugarukamu ezihikire, benzoxazoles 59 zitari zimwe na zimwe zikakorwa. Embeera z‘okugarukamu nizikwatagana n‘ebicweka by‘emirimo bitari bimwe na bimwe, kandi ebicweka by‘omubiri ebitari bimwe na bimwe ebirikukora (bioactive cores) bikakorwa gye, ekirikworeka obushoboorozi bwabyo bw‘ahaiguru bw‘okukora emirimo erikukurataho. Nahabwekyo, tukozire enkora nungi, eyorobi kandi erikukora gye ey’okukora omu bwingi ebirungo bya benzoxazole ebitari bimwe na bimwe kuruga omu katekoli z’obuhangwa omu mbeera za kinyasi turikukoresa ebirungo by’omuhendo mukye.
Ebihandiiko byona ebyatungirwe nari ebyashwijumirwe omu kucondooza oku biri omu kihandiiko eki ekihandiikirwe n‘omu fayiro zaakyo ez‘amakuru g‘okwongyeraho.
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