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Wannan binciken ya ba da rahoton wata hanya mai inganci don haɗa benzoxazoles ta amfani da catechol, aldehyde da ammonium acetate a matsayin abinci ta hanyar haɗakar amsawar ethanol tare da ZrCl4 a matsayin mai haɓaka sinadarai. An samar da jerin benzoxazoles (nau'ikan 59) cikin nasara ta wannan hanyar har zuwa 97%. Sauran fa'idodin wannan hanyar sun haɗa da haɗakarwa mai girma da amfani da iskar oxygen a matsayin wakili mai hana iskar oxygen. Yanayin amsawa mai sauƙi yana ba da damar aiki na gaba, wanda ke sauƙaƙe haɗakar abubuwa daban-daban tare da tsarin da ya dace da ilimin halitta kamar β-lactams da quinoline heterocycles.
Ci gaban sabbin hanyoyin hada kwayoyin halitta wanda zai iya shawo kan iyakokin samun mahadi masu daraja da kuma kara bambancinsu (don bude sabbin fannoni masu yuwuwar amfani) ya jawo hankali sosai a fannin ilimi da masana'antu1,2. Baya ga ingantaccen ingancin wadannan hanyoyin, kyautata muhallin hanyoyin da ake samarwa zai zama babban fa'ida3,4.
Benzoxazoles rukuni ne na mahaɗan heterocyclic waɗanda suka jawo hankali sosai saboda yawan ayyukansu na halitta. An ruwaito cewa irin waɗannan mahaɗan suna da ayyukan hana ƙwayoyin cuta, kariya daga jijiyoyi, hana ciwon daji, maganin rigakafi, maganin kashe ƙwayoyin cuta, maganin rigakafi, da kuma hana kumburi5,6,7,8,9,10,11. Haka kuma ana amfani da su sosai a fannoni daban-daban na masana'antu, ciki har da magunguna, na'urorin jijiyoyi, ilmin kimiya na noma, ligands (don canza ƙarfe), da kimiyyar kayan aiki12,13,14,15,16,17. Saboda keɓancewar sinadarai da kuma iyawarsu, benzoxazoles sun zama muhimman tubalan gini don haɗa ƙwayoyin halitta masu rikitarwa da yawa18,19,20. Abin sha'awa, wasu benzoxazoles suna da muhimman samfura na halitta da ƙwayoyin halitta masu dacewa da magunguna, kamar nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 da neosalvianene (Hoto na 1A)26.
(A) Misalan samfuran halitta da aka samo daga benzoxazole da mahaɗan halitta masu aiki. (B) Wasu hanyoyin halitta na catechols.
Ana amfani da Catechols sosai a fannoni da yawa kamar magunguna, kayan kwalliya da kimiyyar kayan aiki27,28,29,30,31. An kuma nuna cewa Catechols suna da kaddarorin antioxidant da anti-inflammatory, wanda hakan ya sa su zama masu yuwuwar zama wakilai na magani32,33. Wannan kadara ta haifar da amfani da ita wajen haɓaka kayan kwalliya na hana tsufa da kayayyakin kula da fata34,35,36. Bugu da ƙari, an nuna cewa catechols su ne masu tasiri wajen haɗa kwayoyin halitta (Hoto na 1B)37,38. Wasu daga cikin waɗannan catechols suna da yawa a yanayi. Saboda haka, amfani da shi azaman kayan aiki ko kayan farawa don haɗa kwayoyin halitta na iya haɗawa da ƙa'idar sunadarai kore ta "amfani da albarkatun da ake sabuntawa". An ƙirƙiri hanyoyi daban-daban da dama don shirya mahaɗan benzoxazole masu aiki7,39. Ayyukan oxidative na haɗin C(aryl)-OH na catechols yana ɗaya daga cikin hanyoyin da suka fi ban sha'awa da sabbin hanyoyin haɗa benzoxazoles. Misalan wannan hanyar da ake amfani da ita wajen haɗa benzoxazoles sune halayen catechols tare da amines40,41,42,43,44, tare da aldehydes45,46,47, tare da alcohols (ko ethers)48, da kuma tare da ketones, alkenes da alkynes (Hoto na 2A)49. A cikin wannan binciken, an yi amfani da amsawar sassa da yawa (MCR) tsakanin catechol, aldehyde da ammonium acetate don haɗa benzoxazoles (Hoto na 2B). An gudanar da amsawar ta amfani da adadin ZrCl4 mai hana ethanol. Lura cewa ana iya ɗaukar ZrCl4 a matsayin mai hana ethanol kore, mahaɗi ne mara guba [LD50 (ZrCl4, na baki ga beraye) = 1688 mg kg−1] kuma ba a ɗaukarsa a matsayin mai guba sosai50. An kuma yi amfani da masu haɓaka zirconium a matsayin masu haɓaka don haɗa mahaɗan halitta daban-daban. Rashin tsada da kuma kwanciyar hankali ga ruwa da iskar oxygen da suke da shi ya sa su zama masu samar da sinadarai masu kyau a cikin hadakar kwayoyin halitta51.
Domin nemo yanayin amsawar da ta dace, mun zaɓi 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a da gishirin ammonium 3 a matsayin halayen samfuri kuma mun gudanar da halayen a gaban nau'ikan Lewis acid (LA), nau'ikan sinadarai daban-daban da yanayin zafi don haɗa benzoxazole 4a (Tebur 1). Ba a lura da wani samfuri ba idan babu mai kara kuzari (Tebur 1, shigarwar 1). Daga baya, an gwada 5 mol% na nau'ikan Lewis acid daban-daban kamar ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 da MoO3 a matsayin masu kara kuzari a cikin sinadarin EtOH kuma an gano cewa ZrCl4 shine mafi kyau (Tebur 1, shigarwar 2–8). Domin inganta inganci, an gwada sinadarai daban-daban da suka haɗa da dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) da dimethyl sulfoxide (DMSO). Yawan sinadaran da aka gwada ya yi ƙasa da na ethanol (Tebur 1, shigarwar 9-15). Amfani da wasu hanyoyin nitrogen (kamar NH4Cl, NH4CN da (NH4)2SO4) maimakon ammonium acetate bai inganta yawan sinadaran da aka samu ba (Tebur 1, shigarwar 16-18). Ƙarin bincike ya nuna cewa yanayin zafi ƙasa da sama da 60 °C bai inganta yawan sinadaran da aka samu ba (Tebur 1, shigarwar 19 da 20). Lokacin da aka canza nauyin sinadaran da aka samu zuwa 2 da 10 mol%, yawan sinadaran da aka samu ya kai 78% da 92%, bi da bi (Tebur 1, shigarwar 21 da 22). Yawan amfanin ƙasa ya ragu lokacin da aka gudanar da aikin a ƙarƙashin yanayin nitrogen, wanda ke nuna cewa iskar oxygen ta yanayi na iya taka muhimmiyar rawa a cikin aikin (Tebur 1, shigarwar 23). Ƙara yawan ammonium acetate bai inganta sakamakon aikin ba har ma ya rage yawan amfanin ƙasa (Tebur 1, shigarwar 24 da 25). Bugu da ƙari, babu wani ci gaba a cikin aikin aikin da aka samu tare da ƙara yawan catechol (Tebur 1, shigarwar 26).
Bayan tantance yanayin amsawa mafi kyau, an yi nazarin iya aiki da kuma amfani da martanin (Hoto na 3). Tunda alkynes da alkenes suna da ƙungiyoyi masu mahimmanci a cikin haɗin kwayoyin halitta kuma suna iya samun sauƙin daidaitawa, an haɗa wasu abubuwan da aka samo daga benzoxazole tare da alkenes da alkynes (4b–4d, 4f–4g). Ta amfani da 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde azaman substrate na aldehyde (4e), yawan amfanin ya kai 90%. Bugu da ƙari, an haɗa benzoxazoles na alkyl halo waɗanda aka maye gurbinsu a cikin yawan amfanin ƙasa mai yawa, wanda za'a iya amfani da shi don haɗawa da wasu ƙwayoyin halitta da kuma ƙarin rarrabuwa (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde da 4-(benzyloxy)benzaldehyde sun samar da benzoxazoles 4j da 4k masu dacewa a cikin yawan amfanin ƙasa mai yawa, bi da bi. Ta amfani da wannan hanyar, mun sami nasarar haɗa abubuwan da suka samo asali daga benzoxazole (4l da 4m) waɗanda ke ɗauke da ƙwayoyin quinolone53,54,55. An haɗa Benzoxazole 4n wanda ke ɗauke da ƙungiyoyin alkyne guda biyu a cikin kashi 84% na yawan amfanin ƙasa daga benzaldehydes masu maye gurbin 2,4. An haɗa mahaɗin kekuna 4o mai ɗauke da heterocycle na indole cikin nasara a ƙarƙashin yanayi mafi kyau. An haɗa mahaɗin 4p ta amfani da substrate na aldehyde da aka haɗa zuwa ƙungiyar benzonitrile, wanda shine substrate mai amfani don shirya (4q-4r) supramolecules56. Don haskaka yadda wannan hanyar take aiki, an nuna shirye-shiryen ƙwayoyin benzoxazole waɗanda ke ɗauke da ƙwayoyin β-lactam (4q-4r) a ƙarƙashin yanayi mafi kyau ta hanyar amsawar β-lactams, catechol, da ammonium acetate na aldehyde. Waɗannan gwaje-gwajen sun nuna cewa ana iya amfani da sabuwar hanyar haɗin gwiwa don aiwatar da ƙwayoyin hadaddun matakai na ƙarshe.
Domin ƙara nuna sauƙin amfani da juriyar wannan hanyar ga ƙungiyoyin aiki, mun yi nazarin nau'ikan aldehydes masu ƙanshi iri-iri, waɗanda suka haɗa da ƙungiyoyin bayar da electron, ƙungiyoyin janye electron, mahaɗan heterocyclic, da polycyclic aromatic hydrocarbons (Hoto na 4, 4s–4aag). Misali, an canza benzaldehyde zuwa samfurin da ake so (4s) a cikin kashi 92% na yawan amfanin ƙasa. An yi nasarar canza aldehydes masu ƙamshi tare da ƙungiyoyin bayar da electron (gami da -Me, isopropyl, tert-butyl, hydroxyl, da para-SMe) zuwa samfuran da suka dace a cikin kyakkyawan yawan amfanin ƙasa (4t–4x). Substrates na aldehyde masu hana steric na iya samar da samfuran benzoxazole (4y–4aa, 4al) a cikin kyakkyawan yawan amfanin ƙasa zuwa mai kyau. Amfani da benzaldehydes masu maye gurbin meta (4ab, 4ai, 4am) ya ba da damar shirya samfuran benzoxazole a cikin yawan amfanin ƙasa mai yawa. Aldehydes masu halogenated kamar (-F, -CF3, -Cl da Br) sun ba da benzoxazoles masu dacewa (4af, 4ag da 4ai-4an) a cikin yawan amfanin ƙasa mai kyau. Aldehydes tare da ƙungiyoyin cire electron (misali -CN da NO2) suma sun yi aiki da kyau kuma sun ba da samfuran da ake so (4ah da 4ao) a cikin yawan amfanin ƙasa mai yawa.
Jerin martanin da aka yi amfani da su don haɗa aldehydes a da b. a Yanayin amsawa: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) da ZrCl4 (5 mol%) an mayar da su a cikin EtOH (3 mL) a 60 °C na tsawon awanni 6. b Yawan amfanin ya yi daidai da samfurin da aka ware.
Aldehydes masu kama da na polycyclic aromatic kamar 1-naphthaldehyde, anthracene-9-carboxaldehyde da phenanthrene-9-carboxaldehyde na iya samar da samfuran da ake so 4ap-4ar a cikin yawan amfanin ƙasa mai yawa. Aldehydes masu kama da na heterocyclic aromatic daban-daban waɗanda suka haɗa da pyrrole, indole, pyridine, furan da thiophene sun jure yanayin amsawar da kyau kuma suna iya samar da samfuran da suka dace (4as-4az) a cikin yawan amfanin ƙasa mai yawa. An samo Benzoxazole 4aag a cikin yawan amfanin ƙasa mai kashi 52% ta amfani da aldehyde mai kama da na aliphatic.
Yankin amsawa ta amfani da aldehydes na kasuwanci a, b. a Yanayin amsawa: An mayar da martani ga 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) da ZrCl4 (5 mol%) a cikin EtOH (5 mL) a 60 °C na tsawon awanni 4. b Yawan da aka samu ya yi daidai da samfurin da aka ware. c An gudanar da martanin a 80 °C na tsawon awanni 6; d An gudanar da martanin a 100 °C na tsawon awanni 24.
Domin ƙarin bayani game da amfani da wannan hanyar, mun kuma gwada nau'ikan catechols daban-daban da aka maye gurbinsu. Catechols masu maye gurbinsu kamar 4-tert-butylbenzene-1,2-diol da 3-methoxybenzene-1,2-diol sun yi aiki da kyau tare da wannan yarjejeniya, suna samar da benzoxazoles 4aaa–4aac a cikin kashi 89%, 86%, da 57%, bi da bi. An kuma yi nasarar haɗa wasu benzoxazoles masu maye gurbinsu ta amfani da catechols masu maye gurbinsu (4aad–4aaf). Ba a sami wani samfuri ba lokacin da aka yi amfani da catechols masu maye gurbinsu marasa amfani da electron kamar 4-nitrobenzene-1,2-diol da 3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
An yi nasarar haɗa benzoxazole a cikin adadin gram a ƙarƙashin yanayin da aka inganta, kuma an haɗa mahaɗin 4f a cikin kashi 85% na yawan amfanin ƙasa da aka ware (Hoto na 5).
An haɗa benzoxazole 4f a sikelin gram. Yanayin amsawa: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) da ZrCl4 (5 mol%) a cikin EtOH (25 mL) a zafin 60 °C na tsawon awanni 4.
Dangane da bayanan wallafe-wallafe, an gabatar da wata hanyar amsawa mai ma'ana don haɗa benzoxazoles daga catechol, aldehyde, da ammonium acetate a gaban mai haɓaka ZrCl4 (Hoto na 6). Catechol na iya yin chelate zirconium ta hanyar haɗa ƙungiyoyi biyu na hydroxyl don samar da ainihin farkon zagayowar catalytic (I)51. A wannan yanayin, ana iya samar da rabin semiquinone (II) ta hanyar enol-keto tautomerization a cikin hadaddun I58. Ƙungiyar carbonyl da aka samar a matsakaici (II) a bayyane take tana amsawa da ammonium acetate don samar da matsakaicin imine (III) 47. Wani yuwuwar kuma shine imine (III^), wanda aldehyde ya samar tare da ammonium acetate, yana amsawa da ƙungiyar carbonyl don samar da matsakaicin imine-phenol (IV) 59,60. Daga baya, matsakaici (V) na iya yin cyclization na intramolecular40. A ƙarshe, matsakaici V yana oxidize tare da iskar oxygen ta yanayi, yana samar da samfurin da ake so 4 kuma yana sakin hadaddun zirconium don fara zagaye na gaba 61,62.
An sayi dukkan sinadaran da abubuwan da ke narkewa daga hanyoyin kasuwanci. An gano duk samfuran da aka sani ta hanyar kwatantawa da bayanan spectral da wuraren narkewa na samfuran da aka gwada. An rubuta spectra na 1H NMR (400 MHz) da 13C NMR (100 MHz) akan kayan aikin Brucker Avance DRX. An tantance wuraren narkewa akan na'urar Büchi B-545 a cikin babban bututun da aka buɗe. An sa ido kan duk halayen ta hanyar amfani da faranti na siliki (TLC) ta amfani da faranti na silica gel (Silica gel 60 F254, Merck Chemical Company). An gudanar da nazarin abubuwa akan PerkinElmer 240-B Microanalyzer.
An haɗa maganin catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) da ZrCl4 (5 mol%) a cikin ethanol (3.0 mL) a jere a cikin bututun da aka buɗe a cikin wurin wanka mai zafi a digiri 60 Celsius a ƙarƙashin iska na tsawon lokacin da ake buƙata. An sa ido kan ci gaban amsawar ta hanyar amfani da siririn chromatography (TLC). Bayan kammala amsawar, an sanyaya cakuda da aka samu zuwa zafin ɗaki kuma an cire ethanol a ƙarƙashin matsin lamba mai raguwa. An narkar da cakudawar amsawar da EtOAc (3 x 5 mL). Sannan, an busar da haɗin yadudduka na halitta akan Na2SO4 mai hana ruwa kuma an tattara su a cikin vacuo. A ƙarshe, an tsarkake cakuda mai ta hanyar amfani da petroleum ether/EtOAc don samun benzoxazole 4 mai tsabta.
A taƙaice, mun ƙirƙiro wata sabuwar hanya mai sauƙi da kore don haɗa benzoxazoles ta hanyar ƙirƙirar haɗin CN da CO a gaban mai haɓaka sinadarin zirconium. A ƙarƙashin yanayin amsawar da aka inganta, an haɗa benzoxazoles daban-daban guda 59. Yanayin amsawar sun dace da ƙungiyoyi daban-daban na aiki, kuma an haɗa ƙwayoyin halitta da yawa cikin nasara, wanda ke nuna babban yuwuwarsu don aiki mai kyau daga baya. Saboda haka, mun ƙirƙiro wata dabara mai inganci, mai sauƙi kuma mai amfani don samar da nau'ikan benzoxazole daban-daban daga catechols na halitta a ƙarƙashin yanayin kore ta amfani da masu haɓaka sinadarai masu araha.
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