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E whakaatu ana tēnei rangahau i tētahi tikanga tino whai hua mō te hanga benzoxazoles mā te whakamahi i te catechol, te aldehyde me te ammonium acetate hei rauemi whāngai mā te tauhohenga honohono i roto i te ethanol me te ZrCl4 hei whakakorikori. I angitu te hanga o tētahi raupapa benzoxazoles (59 momo) mā tēnei tikanga, ā, tae atu ki te 97% te hua. Ko ētahi atu painga o tēnei huarahi ko te hanga nui me te whakamahi i te hāora hei ākena whakakorikori. Mā ngā āhuatanga tauhohenga ngawari ka taea te mahi i muri mai, e āwhina ana i te hanga o ngā momo hua me ngā hanganga e pā ana ki te koiora pērā i te β-lactams me te quinoline heterocycles.
Kua aro nui te ao mātauranga me te ahumahi ki te whanaketanga o ngā tikanga hou mō te hanga rauropi ka taea te wikitoria i ngā herenga o te whiwhi i ngā matū utu nui, me te whakanui ake i ō rātou kanorau (hei whakatuwhera i ngā wāhi tono hou). 1,2. Haunga te whai huatanga nui o ēnei tikanga, ko te atawhai taiao o ngā huarahi e whakawhanakehia ana he painga nui anō hoki3,4.
Ko ngā benzoxazoles he momo matū heterocyclic kua aro nuitia nā te nui o ā rātou mahi koiora. Kua pūrongohia he mahi patu huakita, tiaki io, ārai matepukupuku, ārai huaketo, ārai mate huakita, ārai harore, me te ārai mumura ēnei matū. E whakamahia whānuitia ana hoki ēnei i roto i ngā mara ahumahi maha tae atu ki ngā rongoā, ngā mahi pūoko, ngā matū ahuwhenua, ngā ligands (mō te whakaterenga whakarewa whakawhiti), me te pūtaiao rauemi12,13,14,15,16,17. Nā ō rātou āhuatanga matū ahurei me te maha o ngā whakamahinga, kua noho ngā benzoxazoles hei poraka hanga nui mō te hanga i ngā ngota waro matatini maha18,19,20. He mea whakamīharo, ko ētahi benzoxazoles he hua taiao nui, ā, he ngota e tika ana mō te rongoā, pērā i te nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 me te neosalvianene (Pikitia 1A)26.
(A) Ngā tauira o ngā hua taiao me ngā matū koiora e ahu mai ana i te benzoxazole. (B) Ētahi puna taiao o ngā catechol.
He whānuitia te whakamahinga o ngā Catechol i roto i ngā mara maha pērā i te rongoā, te whakapaipai me te pūtaiao rauemi27,28,29,30,31. Kua whakaatuhia hoki he āhuatanga antioxidant me te anti-inflammatory ngā Catechol, ā, he pai pea hei rongoā32,33. Nā tēnei āhuatanga i whakamahia ai i roto i te whanaketanga o ngā whakapaipai anti-pakeketanga me ngā hua tiaki kiri34,35,36. I tua atu, kua whakaatuhia ngā catechol he matū whai hua mō te hanga rauropi (Pikitia 1B)37,38. He nui te nui o ētahi o ēnei catechol i roto i te taiao. Nō reira, ko tōna whakamahinga hei rauemi mata, hei rauemi tīmatanga rānei mō te hanga rauropi ka taea te whakatinana i te kaupapa matū matomato o te "whakamahi i ngā rauemi whakahou". He maha ngā huarahi rerekē kua whakawhanakehia hei whakarite i ngā pūhui benzoxazole mahi7,39. Ko te mahi oxidative o te here C(aryl)-OH o ngā catechol tētahi o ngā huarahi tino whakamere me te hou ki te hanga benzoxazoles. Ko ngā tauira o tēnei huarahi i roto i te hanga benzoxazoles ko ngā tauhohenga o ngā catechols me ngā amines40,41,42,43,44, me ngā aldehydes45,46,47, me ngā waipiro (ngā ethers rānei)48, tae atu ki ngā ketones, ngā alkenes me ngā alkynes (Pikitia 2A)49. I roto i tēnei rangahau, i whakamahia he tauhohenga maha-wāhanga (MCR) i waenga i te catechol, te aldehyde me te ammonium acetate mō te hanga benzoxazoles (Pikitia 2B). I mahia te tauhohenga mā te whakamahi i te nui o te ZrCl4 i roto i te whakarewa etanoru. Kia mahara ka taea te whakaaro ko ZrCl4 he kaitahuri waikawa Lewis matomato, he matū iti ake te paitini [LD50 (ZrCl4, ā-waha mō ngā kiore) = 1688 mg kg−1] ā, kāore i te kiia he tino paitini50. Kua whakamahia angitu hoki ngā kaitahuri zirconium hei kaitahuri mō te hanga o ngā momo matū waro. Nā te iti o te utu me te pumau ki te wai me te hāora, he mea whai hua ēnei hei whakakorikori i roto i te hanga rauropi51.
Hei kimi i ngā āhuatanga tauhohenga e tika ana, i whiriwhiria e mātou te 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a me te tote ammonium 3 hei tauira tauhohenga, ā, i whakahaerehia ngā tauhohenga i te aroaro o ngā waikawa Lewis rerekē (LA), ngā whakarewa rerekē me ngā pāmahana hei hanga i te benzoxazole 4a (Ripanga 1). Kāore i kitea he hua i te korenga o te whakakorikori (Ripanga 1, tāurunga 1). I muri mai, 5 mol % o ngā waikawa Lewis rerekē pērā i te ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 me MoO3 i whakamatautauria hei whakakorikori i roto i te whakarewa EtOH, ā, i kitea ko ZrCl4 te mea pai rawa atu (Ripanga 1, tāurunga 2–8). Hei whakapai ake i te whai huatanga, i whakamātauria ngā momo whakarewa tae atu ki te dioxane, te acetonitrile, te ethyl acetate, te dichloroethane (DCE), tetrahydrofuran (THF), te dimethylformamide (DMF) me te dimethyl sulfoxide (DMSO). He iti iho ngā hua o ngā whakarewa katoa i whakamātauria i tērā o te ethanol (Ripanga 1, ngā tāurunga 9–15). Ko te whakamahi i ētahi atu pūtake hauota (pērā i te NH4Cl, NH4CN me te (NH4)2SO4) hei utu mō te ammonium acetate kāore i whakapai ake i te hua tauhohenga (Ripanga 1, ngā tāurunga 16–18). I whakaatuhia e ētahi atu rangahau kāore i whakarei ake te hua tauhohenga i ngā pāmahana i raro iho i te 60 °C me runga ake i te 20). I te whakarerekētanga o te utaina o te whakakorikori ki te 2 me te 10 mol %, ko ngā hua he 78% me te 92%, ia (Ripanga 1, ngā tāurunga 21 me te 22). I heke te hua i te wā i mahia ai te tauhohenga i raro i te hauota hauota, e tohu ana tera pea he mahi nui tā te hāora hau i roto i te tauhohenga (Ripanga 1, tāurunga 23). Kāore te whakanui ake i te nui o te ammonium acetate i whakapai ake i ngā hua o te tauhohenga, ā, i whakaitihia anō hoki te hua (Ripanga 1, ngā tāurunga 24 me te 25). Hei tāpiri, kāore i kitea he whakapainga i roto i te hua tauhohenga me te whakanui ake i te nui o te catechol (Ripanga 1, tāurunga 26).
I muri i te whakatau i ngā āhuatanga tauhohenga tino pai, i tirotirohia te whānui me te whaihua o te tauhohenga (Pikitia 3). Nā te mea he nui ngā rōpū mahi a ngā alkyne me ngā alkene i roto i te hanganga rauropi, ā, he ngāwari ki te whakapūtātanga atu, he maha ngā benzoxazole derivatives i hangaia me ngā alkene me ngā alkyne (4b–4d, 4f–4g). Mā te whakamahi i te 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde hei papa aldehyde (4e), i eke te hua ki te 90%. I tua atu, i hangaia ngā benzoxazoles kua whakakapia ki te alkyl halo i roto i ngā hua teitei, ka taea te whakamahi mō te herenga me ētahi atu ngota me te whakapūtātanga atu (4h–4i) 52. Nā te 4-((4-fluorobenzyl)oxy)benzaldehyde me te 4-(benzyloxy)benzaldehyde i homai ngā benzoxazoles 4j me te 4k e rite ana i roto i ngā hua teitei. Mā te whakamahi i tēnei tikanga, i angitu tā mātou hanga i ngā momo benzoxazole (4l me te 4m) kei roto ngā wāhanga quinolone53,54,55. I hangaia te Benzoxazole 4n kei roto ngā rōpū alkyne e rua i roto i te 84% hua mai i ngā benzaldehyde kua whakakapia ki te 2,4. I angitu te hanga i te pūhui bicyclic 4o kei roto he indole heterocycle i raro i ngā āhuatanga kua arotauhia. I hangaia te pūhui 4p mā te whakamahi i tētahi papa aldehyde i piri ki tētahi rōpū benzonitrile, he papa whai hua mō te whakarite i ngā supramolecules (4q-4r)56. Hei whakaatu i te whai huatanga o tēnei tikanga, i whakaaturia te whakarite i ngā ngota benzoxazole kei roto ngā wāhanga β-lactam (4q–4r) i raro i ngā āhuatanga kua arotauhia mā te tauhohenga o ngā β-lactam kua mahihia e te aldehyde, te catechol, me te ammonium acetate. E whakaatu ana ēnei whakamātautau ka taea te whakamahi i te huarahi hanga hou kua whakawhanakehia mō te mahi-whakaoti-wāhanga o ngā ngota matatini.
Hei whakaatu anō i te whānui me te manawanui o tēnei tikanga ki ngā rōpū mahi, i akohia e mātou ngā momo aldehyde kakara tae atu ki ngā rōpū tuku-irahiko, ngā rōpū tango-irahiko, ngā pūhui heterocyclic, me ngā hauwaiwaro kakara polycyclic (Pikitia 4, 4s–4aag). Hei tauira, i hurihia te benzaldehyde ki te hua e hiahiatia ana (4s) i roto i te 92% o te hua wehe. I angitu te hurihanga o ngā aldehyde kakara me ngā rōpū tuku-irahiko (tae atu ki te -Me, isopropyl, tert-butyl, hydroxyl, me te para-SMe) ki ngā hua e rite ana i roto i ngā hua pai rawa atu (4t–4x). Ka taea e ngā papa aldehyde aukati-stere te whakaputa hua benzoxazole (4y–4aa, 4al) i roto i ngā hua pai ki te pai rawa atu. Mā te whakamahinga o ngā benzaldehyde kua whakakapia ki te meta (4ab, 4ai, 4am) i taea ai te whakarite i ngā hua benzoxazole i roto i ngā hua teitei. Ko ngā aldehyde halogenated pērā i te (-F, -CF3, -Cl me te Br) i homai ngā benzoxazoles e rite ana (4af, 4ag me te 4ai-4an) i roto i ngā hua pai. I pai hoki te tauhohenga o ngā aldehyde me ngā rōpū tango irahiko (hei tauira -CN me te NO2) ā, i homai ngā hua e hiahiatia ana (4ah me te 4ao) i roto i ngā hua teitei.
Ngā raupapa tauhohenga i whakamahia mō te hanga o ngā aldehyde a me b. a Ngā tikanga tauhohenga: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) me ZrCl4 (5 mol%) i tauhohenga ki te EtOH (3 mL) i te 60 °C mō te 6 h. b Ko te hua e rite ana ki te hua kua wehea.
Ka taea e ngā aldehyde aromatic polycyclic pērā i te 1-naphthaldehyde, te anthracene-9-carboxaldehyde me te phenanthrene-9-carboxaldehyde te whakaputa i ngā hua e hiahiatia ana ko te 4ap-4ar me ngā hua teitei. He maha ngā aldehyde aromatic heterocyclic tae atu ki te pyrrole, te indole, te pyridine, te furan me te thiophene i manawanui ki ngā āhuatanga tauhohenga, ā, ka taea te whakaputa i ngā hua e rite ana (4as-4az) me ngā hua teitei. I whiwhihia te Benzoxazole 4aag i te hua 52% mā te whakamahi i te aldehyde aliphatic e rite ana.
Rohe tauhohenga e whakamahi ana i ngā aldehyde arumoni a, b. a Ngā tikanga tauhohenga: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) me ZrCl4 (5 mol %) i tauhohenga ki te EtOH (5 mL) i te 60 °C mō te 4 h. b Ko te hua e rite ana ki te hua i wehea. c I mahia te tauhohenga i te 80 °C mō te 6 h; d I mahia te tauhohenga i te 100 °C mō te 24 h.
Hei whakaatu anō i te whānui me te whaihua o tēnei tikanga, i whakamatauria hoki e mātou ngā momo catechol kua whakakapia. I pai te tauhohenga o ngā catechol monosubstituted pērā i te 4-tert-butylbenzene-1,2-diol me te 3-methoxybenzene-1,2-diol ki tēnei tikanga, ā, i puta ai ngā benzoxazoles 4aaa–4aac i roto i ngā hua 89%, 86%, me te 57%. I angitu hoki te hanga o ētahi benzoxazoles polysubstituted mā te whakamahi i ngā catechol polysubstituted e rite ana (4aad–4aaf). Kāore i puta he hua i te whakamahinga o ngā catechol kua whakakapia kāore i te whai irahiko pērā i te 4-nitrobenzene-1,2-diol me te 3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
I oti pai te hanga o te benzoxazole i roto i ngā rahinga karamu i raro i ngā āhuatanga kua arotauhia, ā, i hangaia te matū 4f i roto i te 85% o te hua wehe (Pikitia 5).
Te hanganga tauine-karamu o te benzoxazole 4f. Ngā āhuatanga tauhohenga: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) me ZrCl4 (5 mol%) i tauhohengahia ki te EtOH (25 mL) i te 60 °C mō te 4 hāora.
I runga i ngā raraunga tuhinga, kua whakaarohia he tikanga tauhohenga whaitake mō te hanga benzoxazoles mai i te catechol, aldehyde, me te ammonium acetate i te aroaro o te whakakorikori ZrCl4 (Pikitia 6). Ka taea e te Catechol te whakakorikori i te zirconium mā te whakarite i ngā rōpū hydroxyl e rua hei hanga i te matua tuatahi o te huringa whakakorikori (I)51. I tēnei take, ka taea te hanga i te wāhanga semiquinone (II) mā te tautomerization enol-keto i roto i te matatini I58. Ko te rōpū carbonyl i hangaia i roto i te takawaenga (II) te āhua nei ka tauhohe ki te ammonium acetate hei hanga i te takawaenga imine (III) 47. Ko tētahi atu pea ko te imine (III^), i hangaia e te tauhohenga o te aldehyde me te ammonium acetate, ka tauhohe ki te rōpū carbonyl hei hanga i te takawaenga imine-phenol (IV) 59,60. Muri iho, ka taea e te takawaenga (V) te whai i te huringa intramolecular40. Hei whakamutunga, ka waikurahia te takawaenga V ki te hāora hau, ka puta te hua e hiahiatia ana 4 ka tukuna te matatini zirconium hei tīmata i te huringa e whai ake nei61,62.
I hokona mai ngā matū me ngā whakarewa katoa mai i ngā puna arumoni. I tautuhia ngā hua katoa e mōhiotia ana mā te whakataurite ki ngā raraunga hihi me ngā ira rewa o ngā tauira i whakamatautauria. I tuhia ngā hihi 1H NMR (400 MHz) me te 13C NMR (100 MHz) ki runga i te taputapu Brucker Avance DRX. I whakatauhia ngā ira rewa ki runga i te taputapu Büchi B-545 i roto i te capillary tuwhera. I aro turukihia ngā tauhohenga katoa mā te chromatography paparanga-angiangi (TLC) mā te whakamahi i ngā pereti silica gel (Silica gel 60 F254, Merck Chemical Company). I mahia te tātari huānga ki runga i te PerkinElmer 240-B Microanalyzer.
I whakaohokia te otinga o te catechol (1.0 mmol), te aldehyde (1.0 mmol), te ammonium acetate (1.0 mmol) me te ZrCl4 (5 mol %) i roto i te etanoru (3.0 mL) i roto i tētahi ngongo tuwhera i roto i tētahi kaukau hinu i te 60 °C i raro i te hau mō te wā e hiahiatia ana. I aro turukihia te ahunga whakamua o te tauhohenga mā te chromatography paparanga angiangi (TLC). I muri i te otinga o te tauhohenga, i whakamataohia te ranunga hua ki te pāmahana rūma, ā, i tangohia te etanoru i raro i te pēhanga whakaiti. I waimehahia te ranunga tauhohenga ki te EtOAc (3 x 5 mL). Kātahi ka whakamarokehia ngā paparanga rauropi kua whakakotahi ki runga i te Na2SO4 anhydrous, ā, i whakatōkia ki roto i te korehau. Hei whakamutunga, i purea te ranunga mata mā te chromatography pou mā te whakamahi i te petroleum ether/EtOAc hei eluent hei hanga i te benzoxazole 4 parakore.
Hei whakarāpopototanga, kua whakawhanakehia e mātou tētahi tikanga hou, ngāwari, ā, matomato hoki mō te hanga benzoxazoles mā te hanganga raupapa o ngā hononga CN me CO i te aroaro o te whakakorikori zirconium. I raro i ngā tikanga tauhohenga kua arotauhia, e 59 ngā benzoxazoles rerekē i hangaia. He hototahi ngā tikanga tauhohenga ki ngā rōpū mahi rerekē, ā, he maha ngā matua koiora i hangaia angitu, e tohu ana i tō rātou pūmanawa teitei mō te mahi i muri mai. Nō reira, kua whakawhanakehia e mātou tētahi rautaki whai hua, māmā, ā, whai hua hoki mō te whakaputanga nui o ngā momo benzoxazole derivatives mai i ngā catechols tūturu i raro i ngā tikanga matomato mā te whakamahi i ngā whakakorikori iti te utu.
Kei roto i tēnei tuhinga kua whakaputaina me ōna kōnae Mōhiohio Tāpiri ngā raraunga katoa i kohia, i tātaritatia rānei i tēnei rangahau.
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