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Hōʻike kēia haʻawina i kahi ʻano hana kūpono loa no ka synthesis o benzoxazoles me ka hoʻohana ʻana i ka catechol, aldehyde a me ka ammonium acetate ma ke ʻano he feedstock ma o ka hoʻopili ʻana i ka ethanol me ZrCl4 ma ke ʻano he catalyst. Ua hoʻohui maikaʻi ʻia kahi moʻo o benzoxazoles (59 mau ʻano) e kēia ʻano hana i nā hua a hiki i ka 97%. ʻO nā pono ʻē aʻe o kēia ʻano hana e pili ana i ka synthesis nui a me ka hoʻohana ʻana i ka oxygen ma ke ʻano he oxidizing agent. ʻAe nā kūlana hopena akahai i ka hana ma hope, kahi e hoʻomaʻamaʻa ai i ka synthesis o nā derivatives like ʻole me nā ʻano pili biologically e like me β-lactams a me quinoline heterocycles.
ʻO ka hoʻomohala ʻana i nā ʻano hana hou o ka synthesis organik e hiki ke lanakila i nā palena i ka loaʻa ʻana o nā hui waiwai nui a hoʻonui i ko lākou ʻano like ʻole (e wehe i nā wahi kūpono hou o ka noi) ua huki nui i ka manaʻo ma nā kula nui a me nā ʻoihana1,2. Ma waho aʻe o ka pono kiʻekiʻe o kēia mau ʻano hana, ʻo ke aloha kaiapuni o nā ʻano hana e hoʻomohala ʻia nei he pono nui nō hoʻi3,4.
ʻO Benzoxazoles kahi papa o nā hui heterocyclic i huki nui ʻia ka nānā ma muli o kā lākou mau hana olaola waiwai. Ua hōʻike ʻia kēlā mau hui he mau hana antimicrobial, neuroprotective, anticancer, antiviral, antibacterial, antifungal, a me nā hana anti-inflammatory5,6,7,8,9,10,11. Hoʻohana nui ʻia lākou i nā ʻano ʻoihana like ʻole e like me nā lāʻau lapaʻau, sensorics, agrochemistry, ligands (no ka catalysis metala hoʻololi), a me ka ʻepekema mea12,13,14,15,16,17. Ma muli o ko lākou mau waiwai kemika kū hoʻokahi a me ka versatility, ua lilo nā benzoxazoles i mau poloka hale koʻikoʻi no ka synthesis o nā molekala organik paʻakikī he nui18,19,20. ʻO ka mea hoihoi, ʻo kekahi mau benzoxazoles he mau huahana kūlohelohe koʻikoʻi a me nā molekala pili pharmacologically, e like me nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 a me neosalvianene (Kiʻi 1A)26.
(A) Nā laʻana o nā huahana kūlohelohe i hoʻokumu ʻia i ka benzoxazole a me nā hui bioactive. (B) Kekahi mau kumu kūlohelohe o nā catechols.
Hoʻohana nui ʻia nā Catechols ma nā ʻano he nui e like me nā lāʻau lapaʻau, nā mea hoʻonani a me ka ʻepekema mea27,28,29,30,31. Ua hōʻike ʻia hoʻi nā Catechols he mau waiwai antioxidant a me anti-inflammatory, e lilo ana lākou i mau moho kūpono e like me nā mea hoʻōla32,33. Ua alakaʻi kēia waiwai i kona hoʻohana ʻia ʻana i ka hoʻomohala ʻana i nā mea hoʻonani anti-aging a me nā huahana mālama ʻili34,35,36. Eia kekahi, ua hōʻike ʻia nā catechols he mau mea mua kūpono no ka synthesis organik (Kiʻi 1B)37,38. Nui ka nui o kekahi o kēia mau catechols ma ke ʻano. No laila, ʻo kona hoʻohana ʻana ma ke ʻano he mea maka a mea hoʻomaka paha no ka synthesis organik hiki ke hoʻokomo i ke kumumanaʻo kemika ʻōmaʻomaʻo o ka "hoʻohana ʻana i nā kumuwaiwai hou". Ua hoʻomohala ʻia kekahi mau ala like ʻole e hoʻomākaukau i nā hui benzoxazole functionalized7,39. ʻO ka hana oxidative o ka pilina C (aryl) -OH o nā catechols kekahi o nā ala hoihoi a hou loa i ka synthesis o benzoxazoles. ʻO nā hiʻohiʻona o kēia ʻano hana i ka synthesis o benzoxazoles he mau hopena o nā catechols me nā amines40,41,42,43,44, me nā aldehydes45,46,47, me nā alcohols (a i ʻole ethers)48, a me nā ketones, alkenes a me nā alkynes (Kiʻi 2A)49. Ma kēia haʻawina, ua hoʻohana ʻia kahi hopena multicomponent (MCR) ma waena o catechol, aldehyde a me ammonium acetate no ka synthesis o benzoxazoles (Kiʻi 2B). Ua hoʻokō ʻia ka hopena me ka hoʻohana ʻana i ka nui catalytic o ZrCl4 i loko o ka ethanol solvent. E hoʻomaopopo he hiki ke manaʻo ʻia ʻo ZrCl4 he mea hoʻonui waikawa Lewis ʻōmaʻomaʻo, he hui ʻawaʻawa ʻole ia [LD50 (ZrCl4, waha no nā ʻiole) = 1688 mg kg−1] a ʻaʻole i manaʻo ʻia he ʻawaʻawa loa50. Ua hoʻohana pono ʻia nā mea hoʻonui Zirconium ma ke ʻano he mea hoʻonui no ka synthesis o nā hui organik like ʻole. ʻO ko lākou kumukūʻai haʻahaʻa a me ke kūpaʻa kiʻekiʻe i ka wai a me ka oxygen e hoʻolilo iā lākou i mau mea hoʻoikaika kūpono i ka synthesis organik51.
No ka loaʻa ʻana o nā kūlana hopena kūpono, ua koho mākou iā 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a a me ka paʻakai ammonium 3 ma ke ʻano he mau hopena hoʻohālike a ua hoʻokō i nā hopena i ke alo o nā waikawa Lewis like ʻole (LA), nā mea hoʻoheheʻe like ʻole a me nā mahana e synthesize i ka benzoxazole 4a (Papa 1). ʻAʻohe huahana i ʻike ʻia i ka loaʻa ʻole o ka mea hoʻoulu (Papa 1, komo 1). Ma hope mai, ua hoʻāʻo ʻia he 5 mol% o nā waikawa Lewis like ʻole e like me ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 a me MoO3 ma ke ʻano he mau mea hoʻoulu i loko o ka mea hoʻoheheʻe EtOH a ua ʻike ʻia ʻo ZrCl4 ka mea maikaʻi loa (Papa 1, komo 2-8). No ka hoʻomaikaʻi ʻana i ka pono, ua hoʻāʻo ʻia nā mea hoʻoheheʻe like ʻole e like me ka dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) a me dimethyl sulfoxide (DMSO). ʻOi aku ka haʻahaʻa o nā hua o nā mea hoʻoheheʻe a pau i hoʻāʻo ʻia ma mua o ka ethanol (Papa 1, nā komo 9-15). ʻO ka hoʻohana ʻana i nā kumu naikokene ʻē aʻe (e like me NH4Cl, NH4CN a me (NH4)2SO4) ma kahi o ka ammonium acetate ʻaʻole i hoʻomaikaʻi i ka hua o ka hopena (Papa 1, nā komo 16-18). Ua hōʻike ʻia nā haʻawina hou aʻe ʻaʻole i hoʻonui nā mahana ma lalo a ma luna o 60 °C i ka hua o ka hopena (Papa 1, nā komo 19 a me 20). I ka wā i hoʻololi ʻia ai ka hoʻouka ʻana o ka catalyst i 2 a me 10 mol%, ʻo nā hua he 78% a me 92%, kēlā me kēia (Papa 1, nā komo 21 a me 22). Ua emi ka hua i ka wā i hana ʻia ai ka hopena ma lalo o ka lewa naikokene, e hōʻike ana he kuleana koʻikoʻi paha ka oxygen lewa i ka hopena (Papa 1, komo 23). ʻAʻole i hoʻomaikaʻi ka hoʻonui ʻana i ka nui o ka ammonium acetate i nā hopena hopena a ua hoʻemi pū i ka hua (Papa 1, nā komo 24 a me 25). Eia kekahi, ʻaʻohe hoʻomaikaʻi ʻana i ka hua hopena i ʻike ʻia me ka hoʻonui ʻana i ka nui o ka catechol (Papa 1, komo 26).
Ma hope o ka hoʻoholo ʻana i nā kūlana hopena kūpono, ua aʻo ʻia ka versatility a me ka hoʻohana ʻana o ka hopena (Kiʻi 3). ʻOiai he mau hui hana koʻikoʻi ko nā alkynes a me nā alkenes i ka synthesis organik a maʻalahi hoʻi e hoʻololi hou ʻia, ua synthesized ʻia kekahi mau benzoxazole derivatives me nā alkenes a me nā alkynes (4b–4d, 4f–4g). Ma ka hoʻohana ʻana i ka 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde ma ke ʻano he substrate aldehyde (4e), ua hōʻea ka hua i 90%. Eia kekahi, ua synthesized ʻia nā benzoxazoles i hoʻololi ʻia me nā alkyl halo i nā hua kiʻekiʻe, hiki ke hoʻohana ʻia no ka ligation me nā molekala ʻē aʻe a me ka derivatization hou aʻe (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde a me 4-(benzyloxy)benzaldehyde i hāʻawi i nā benzoxazoles 4j a me 4k e pili ana i nā hua kiʻekiʻe, kēlā me kēia. Ma ka hoʻohana ʻana i kēia ʻano hana, ua hoʻohui maikaʻi mākou i nā benzoxazole derivatives (4l a me 4m) e loaʻa ana nā moieties quinolone53,54,55. Ua hoʻohui ʻia ʻo Benzoxazole 4n e loaʻa ana nā hui alkyne ʻelua ma ka 84% yield mai 2,4-substituted benzaldehydes. Ua hoʻohui maikaʻi ʻia ka hui bicyclic 4o e loaʻa ana kahi indole heterocycle ma lalo o nā kūlana i hoʻonui ʻia. Ua hoʻohui ʻia ka hui 4p me ka hoʻohana ʻana i kahi substrate aldehyde i hoʻopili ʻia i kahi hui benzonitrile, he substrate pono ia no ka hoʻomākaukau ʻana o (4q-4r) supramolecules56. No ka hōʻike ʻana i ka hiki ke hoʻohana ʻia o kēia ʻano hana, ua hōʻike ʻia ka hoʻomākaukau ʻana o nā mole benzoxazole e loaʻa ana nā moieties β-lactam (4q–4r) ma lalo o nā kūlana i hoʻonui ʻia ma o ka hopena o nā β-lactams aldehyde-functionalized, catechol, a me ammonium acetate. Hōʻike kēia mau hoʻokolohua e hiki ke hoʻohana ʻia ke ʻano synthetic i hoʻomohala hou ʻia no ka hana hope o nā mole paʻakikī.
No ka hōʻike hou aku i ka versatility a me ka hoʻomanawanui o kēia ʻano hana i nā hui hana, ua aʻo mākou i nā ʻano aldehydes aromatic like ʻole me nā hui hāʻawi electron, nā hui electron-withdrawing, nā hui heterocyclic, a me nā polycyclic aromatic hydrocarbons (Kiʻi 4, 4s–4aag). No ka laʻana, ua hoʻololi ʻia ʻo benzaldehyde i ka huahana i makemake ʻia (4s) ma ka 92% isolated yield. Ua hoʻololi pono ʻia nā aldehydes aromatic me nā hui hāʻawi electron (me -Me, isopropyl, tert-butyl, hydroxyl, a me para-SMe) i nā huahana like i nā hua maikaʻi loa (4t–4x). Hiki i nā substrates aldehyde i hoʻopaʻa ʻia ke hana i nā huahana benzoxazole (4y–4aa, 4al) i nā hua maikaʻi a maikaʻi loa. ʻO ka hoʻohana ʻana i nā benzaldehydes meta-substituted (4ab, 4ai, 4am) i ʻae i ka hoʻomākaukau ʻana o nā huahana benzoxazole i nā hua kiʻekiʻe. ʻO nā aldehydes halogenated e like me (-F, -CF3, -Cl a me Br) i hāʻawi i nā benzoxazoles like (4af, 4ag a me 4ai-4an) i nā hua kūpono. Ua pane maikaʻi pū nā Aldehydes me nā hui huki uila (e laʻa me -CN a me NO2) a hāʻawi i nā huahana i makemake ʻia (4ah a me 4ao) i nā hua kiʻekiʻe.
Nā moʻo hopena i hoʻohana ʻia no ka hana ʻana o nā aldehydes a a me b. a Nā kūlana hopena: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) a me ZrCl4 (5 mol%) i hana ʻia ma EtOH (3 mL) ma 60 °C no 6 h. b Pili ka hua i ka huahana i hoʻokaʻawale ʻia.
ʻO nā polycyclic aromatic aldehydes e like me 1-naphthaldehyde, anthracene-9-carboxaldehyde a me phenanthrene-9-carboxaldehyde hiki ke hoʻopuka i nā huahana i makemake ʻia 4ap-4ar i nā hua kiʻekiʻe. ʻO nā ʻano heterocyclic aromatic aldehydes e like me pyrrole, indole, pyridine, furan a me thiophene i ʻae maikaʻi i nā kūlana hopena a hiki ke hoʻopuka i nā huahana like (4as-4az) i nā hua kiʻekiʻe. Ua loaʻa ʻo Benzoxazole 4aag ma ka 52% hua me ka hoʻohana ʻana i ka aliphatic aldehyde like.
ʻĀpana hopena e hoʻohana ana i nā aldehydes kalepa a, b. a Nā kūlana hopena: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) a me ZrCl4 (5 mol%) i hana ʻia ma EtOH (5 mL) ma 60 °C no 4 h. b Pili ka hua i ka huahana i hoʻokaʻawale ʻia. c Ua hana ʻia ka hopena ma 80 °C no 6 h; d Ua hana ʻia ka hopena ma 100 °C no 24 h.
I mea e hoʻākāka hou aku ai i ka versatility a me ka hoʻohana ʻana o kēia ʻano hana, ua hoʻāʻo pū mākou i nā catechols pani like ʻole. ʻO nā catechols monosubstituted e like me 4-tert-butylbenzene-1,2-diol a me 3-methoxybenzene-1,2-diol i pane maikaʻi me kēia protocol, e hāʻawi ana i nā benzoxazoles 4aaa–4aac ma 89%, 86%, a me 57% mau hua, kēlā me kēia. Ua hoʻohui maikaʻi ʻia kekahi mau benzoxazoles polysubstituted me ka hoʻohana ʻana i nā catechols polysubstituted like (4aad–4aaf). ʻAʻohe huahana i loaʻa i ka wā i hoʻohana ʻia ai nā catechols pani electron-deficient e like me 4-nitrobenzene-1,2-diol a me 3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
Ua hoʻokō pono ʻia ka synthesis o benzoxazole i nā nui gram ma lalo o nā kūlana i hoʻonui ʻia, a ua synthesized ʻia ka hui 4f ma ka 85% i hoʻokaʻawale ʻia (Kiʻi 5).
Hana ʻia ʻana o ka benzoxazole 4f ma ke ʻano Gram. Nā kūlana hopena: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) a me ZrCl4 (5 mol%) i hana ʻia ma EtOH (25 mL) ma 60 °C no 4 h.
Ma muli o ka ʻikepili palapala, ua hāpai ʻia kahi ʻano hana kūpono no ka synthesis o benzoxazoles mai catechol, aldehyde, a me ammonium acetate i ke alo o ZrCl4 catalyst (Kiʻi 6). Hiki i ka Catechol ke chelate i ka zirconium ma ka hoʻonohonoho ʻana i ʻelua mau hui hydroxyl e hana i ke kumu mua o ka pōʻaiapuni catalytic (I)51. I kēia hihia, hiki ke hoʻokumu ʻia ka semiquinone moiety (II) ma o ka enol-keto tautomerization i loko o ka complex I58. ʻIke ʻia ka hui carbonyl i hoʻokumu ʻia ma waena (II) e hana me ka ammonium acetate e hana i ka imine waena (III) 47. ʻO kekahi mea hiki ke hana ʻia ʻo ka imine (III^), i hoʻokumu ʻia e ka hopena o ka aldehyde me ka ammonium acetate, e hana me ka hui carbonyl e hana i ka imine-phenol waena (IV) 59,60. Ma hope mai, hiki i ka waena (V) ke hana i ka cyclization intramolecular40. ʻO ka hope loa, ua oxidized ʻia ka waena V me ka oxygen atmospheric, e hāʻawi ana i ka huahana i makemake ʻia 4 a hoʻokuʻu i ka zirconium complex e hoʻomaka i ka pōʻaiapuni aʻe61,62.
Ua kūʻai ʻia nā reagents a me nā solvents āpau mai nā kumu kalepa. Ua ʻike ʻia nā huahana i ʻike ʻia ma ka hoʻohālikelike ʻana me ka ʻikepili spectral a me nā kiko heheʻe o nā laʻana i hoʻāʻo ʻia. Ua hoʻopaʻa ʻia nā spectra 1H NMR (400 MHz) a me 13C NMR (100 MHz) ma kahi mea hana Brucker Avance DRX. Ua hoʻoholo ʻia nā kiko heheʻe ma kahi mea hana Büchi B-545 i loko o kahi capillary hāmama. Ua nānā ʻia nā hopena āpau e ka chromatography papa lahilahi (TLC) me ka hoʻohana ʻana i nā papa silica gel (Silica gel 60 F254, Merck Chemical Company). Ua hana ʻia ka loiloi Elemental ma kahi PerkinElmer 240-B Microanalyzer.
Ua hoʻoulu pinepine ʻia kahi hopena o ka catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) a me ZrCl4 (5 mol%) i loko o ka ethanol (3.0 mL) i loko o kahi ʻōmole hāmama i loko o kahi ʻauʻau aila ma 60 °C ma lalo o ka ea no ka manawa i koi ʻia. Ua nānā ʻia ka holomua o ka hopena e ka chromatography papa lahilahi (TLC). Ma hope o ka pau ʻana o ka hopena, ua hoʻomaʻalili ʻia ka hui hopena i ka mahana o ka lumi a ua wehe ʻia ka ethanol ma lalo o ke kaomi i hoʻemi ʻia. Ua hoʻoheheʻe ʻia ka hui hopena me EtOAc (3 x 5 mL). A laila, ua hoʻomaloʻo ʻia nā papa organik i hui pū ʻia ma luna o ka Na2SO4 anhydrous a ua hoʻopaʻa ʻia i loko o ka vacuum. ʻO ka hope loa, ua hoʻomaʻemaʻe ʻia ka hui maka e ka chromatography kolamu me ka hoʻohana ʻana i ka petroleum ether/EtOAc ma ke ʻano he eluent e hāʻawi i ka benzoxazole 4 maʻemaʻe.
I ka hōʻuluʻulu manaʻo, ua hoʻomohala mākou i kahi protocol hou, ʻoluʻolu a ʻōmaʻomaʻo no ka synthesis o benzoxazoles ma o ka hoʻokumu ʻana o nā pilina CN a me CO i ke alo o ka mea hoʻoulu zirconium. Ma lalo o nā kūlana hana i hoʻomaikaʻi ʻia, ua synthesized ʻia he 59 mau benzoxazoles like ʻole. Hoʻohālikelike nā kūlana hana me nā hui hana like ʻole, a ua synthesized kūleʻa kekahi mau ʻiʻo bioactive, e hōʻike ana i ko lākou hiki ke kiʻekiʻe no ka hana ʻana ma hope. No laila, ua hoʻomohala mākou i kahi hoʻolālā kūpono, maʻalahi a kūpono hoʻi no ka hana nui ʻana o nā ʻano benzoxazole derivatives mai nā catechols kūlohelohe ma lalo o nā kūlana ʻōmaʻomaʻo me ka hoʻohana ʻana i nā mea hoʻoulu haʻahaʻa.
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