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Chidzidzo ichi chinoshuma nzira inoshanda zvikuru yekugadzira benzoxazoles uchishandisa catechol, aldehyde uye ammonium acetate se feedstock kuburikidza ne coupling reaction mu ethanol neZrCl4 se catalyst. Mabenzoxazoles akatevedzana (mhando 59) akagadzirwa zvinobudirira nenzira iyi muzvibereko zvinosvika 97%. Zvimwe zvakanakira nzira iyi zvinosanganisira kugadzira kukuru uye kushandiswa kwe oxygen se oxidizing agent. Mamiriro ekuita zvinyoro anobvumira kushanda kunotevera, izvo zvinoita kuti zvive nyore kugadzira zvinhu zvakasiyana-siyana zvine maumbirwo akakodzera biology senge β-lactams uye quinoline heterocycles.
Kugadzirwa kwenzira itsva dzekugadzira organic dzinogona kukunda zvipingamupinyi pakuwana makemikari ane mutengo wakakwira uye kuwedzera kusiyana kwawo (kuvhura nzvimbo itsva dzinogona kushandiswa) kwakakwezva kutariswa kukuru muzvikoro nemumaindasitiri1,2. Kuwedzera pakushanda kwakanyanya kwenzira idzi, hushamwari hwenzvimbo dziri kugadzirwa huchavawo mukana mukuru3,4.
Benzoxazoles iboka remakemikari eheterocyclic akakwezva vanhu vakawanda nekuda kwebasa rawo rakapfuma rezvehupenyu. Mishonga yakadaro inonzi ine mabasa ekurwisa utachiona, kudzivirira tsinga, kurwisa kenza, antiviral, antibacterial, antifungal, uye anti-inflammatory5,6,7,8,9,10,11. Inoshandiswawo zvakanyanya muminda yakasiyana-siyana yeindasitiri inosanganisira mishonga, sensorics, agrochemistry, ligands (yekuchinja metal catalysis), uye materials science12,13,14,15,16,17. Nekuda kwehunhu hwayo hwemakemikari hwakasiyana uye kushanduka-shanduka, benzoxazoles dzave zvinhu zvakakosha zvekuvaka mukugadzirwa kwemamorekuru akawanda akaomarara eorganic18,19,20. Zvinofadza kuti, mamwe mabenzoxazoles zvigadzirwa zvechisikigo zvakakosha uye mamorekuru ane chekuita nemakemikari, akadai se nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 uye neosalvianene (Mufananidzo 1A)26.
(A) Mienzaniso yezvigadzirwa zvechisikigo zvakagadzirwa nebenzoxazole uye zvinhu zvinoshanda mumuviri. (B) Zvimwe zvinhu zvechisikigo zvinobva mumakatekesi.
MaCatechol anoshandiswa zvakanyanya muminda yakawanda yakadai semishonga, zvizoro uye sainzi yezvinhu27,28,29,30,31. MaCatechol akaratidzwawo kuti ane hunhu hweantioxidant uye hwekudzivirira kuzvimba, zvichiita kuti ave anogona kushandiswa semishonga yekurapa32,33. Hunhu uhwu hwakaita kuti ishandiswe mukugadzira zvizoro zvekudzivirira kukwegura uye zvigadzirwa zvekuchengetedza ganda34,35,36. Uyezve, maCatechol akaratidzwa kuti anobatsira pakugadzira organic synthesis (Mufananidzo 1B)37,38. Mamwe emaCatechol aya anowanikwa zvakanyanya. Nokudaro, kushandiswa kwawo sechinhu chisina kubikwa kana chekutanga chekugadzira organic synthesis kunogona kutevedzera musimboti we "green chemistry" we "kushandisa zviwanikwa zvinodzokororwa". Nzira dzakasiyana-siyana dzakagadzirwa kugadzirira functionalized benzoxazole compounds7,39. Oxidative functionalization yeC(aryl)-OH bond yecatechols ndeimwe yenzira dzinonakidza uye itsva dzekugadzira benzoxazoles. Mienzaniso yenzira iyi mukugadzirwa kwebenzoxazoles maitiro emakatekesi nemaamines40,41,42,43,44, ane aldehydes45,46,47, ane alcohols (kana ethers)48, pamwe chete nemaketones, alkenes uye alkynes (Mufananidzo 2A)49. Muchidzidzo ichi, multicomponent reaction (MCR) pakati pecatechol, aldehyde uye ammonium acetate yakashandiswa mukugadzirwa kwebenzoxazoles (Mufananidzo 2B). Maitiro acho akaitwa uchishandisa catalytic amount yeZrCl4 mu ethanol solvent. Cherechedza kuti ZrCl4 inogona kutorwa se green Lewis acid catalyst, i compound isina chepfu [LD50 (ZrCl4, inonwiwa nemakonzo) = 1688 mg kg−1] uye haionekwi seine chepfu yakanyanya50. Zirconium catalysts dzakashandiswawo zvinobudirira se catalysts mukugadzirwa kwe organic compounds dzakasiyana-siyana. Kudhura kwadzo kwakaderera uye kugadzikana kwakanyanya mumvura neokisijeni zvinoita kuti dzive catalysts dzinovimbisa mukugadzirwa kwezvinhu zvakasikwa51.
Kuti tiwane mamiriro akakodzera ekuita, takasarudza 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a uye ammonium salt 3 senzira dzekuita uye takaita nzira dzekuita nadzo pamberi peLewis acids (LA) dzakasiyana, solvents dzakasiyana uye tembiricha yekugadzira benzoxazole 4a (Tafura 1). Hapana chigadzirwa chakaonekwa pasina catalyst (Tafura 1, pinda 1). Zvadaro, 5 mol % yemaLewis acids akasiyana akadai seZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 uye MoO3 akaedzwa se catalysts muEtOH solvent uye ZrCl4 yakawanikwa iriyo yakanakisa (Tafura 1, pinda 2–8). Kuti zvivandudzwe kushanda zvakanaka, mishonga yakasiyana-siyana inonyungudutsa yakaedzwa inosanganisira dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) uye dimethyl sulfoxide (DMSO). Goho remishonga yese inonyungudutsa yakaedzwa raive rakaderera pane reethanol (Tafura 1, zvinyorwa 9–15). Kushandisa mamwe nitrogen sources (akadai seNH4Cl, NH4CN uye (NH4)2SO4) pachinzvimbo cheammonium acetate hakuna kuwedzera goho re reaction (Tafura 1, zvinyorwa 16–18). Zvimwe zvidzidzo zvakaratidza kuti tembiricha dziri pasi nepamusoro pe60 °C hadzina kuwedzera goho re reaction (Tafura 1, zvinyorwa 19 na20). Apo catalyst loading yakachinjwa kuita 2 na10 mol %, goho raive 78% na92%, zvichiteerana (Tafura 1, zvinyorwa 21 na22). Goho rakaderera apo reaction yakaitwa pasi pemhepo ine nitrogen, zvichiratidza kuti oxygen yemumhepo inogona kuita basa guru mu reaction (Tafura 1, chitsauko 23). Kuwedzera huwandu hweammonium acetate hakuna kuvandudza mhedzisiro ye reaction uye kwakatoderedza goho (Tafura 1, chitsauko 24 ne25). Pamusoro pezvo, hapana kuvandudzika mu reaction good yakaonekwa nekuwedzera kwehuwandu hwecatechol (Tafura 1, chitsauko 26).
Mushure mekuona mamiriro ekuita zvakanaka, kushanduka-shanduka uye kushanda kwekuita kwacho kwakadzidzwa (Mufananidzo 3). Sezvo maalkynes nemaalkenes aine mapoka akakosha ekushanda mukugadzirwa kweorganic uye zviri nyore kuti zvibviswe zvakanyanya, mabenzoxazole derivatives akati wandei akagadzirwa nealkenes nemaalkynes (4b–4d, 4f–4g). Uchishandisa 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde se aldehyde substrate (4e), goho rakasvika 90%. Pamusoro pezvo, alkyl halo-substituted benzoxazoles akagadzirwa mu goho guru, iro rinogona kushandiswa pakubatanidza nemamwe mamorekuru uye kuwedzera derivatization (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde uye 4-(benzyloxy)benzaldehyde zvakapa benzoxazoles dzinoenderana 4j uye 4k mu goho guru, zvichiteerana. Tichishandisa nzira iyi, takabudirira kugadzira benzoxazole derivatives (4l ne4m) ine quinolone moieties53,54,55. Benzoxazole 4n ine mapoka maviri ealkyne yakagadzirwa ne84% goho kubva ku2,4-substituted benzaldehydes. Bicyclic compound 4o ine indole heterocycle yakagadzirwa zvakanaka pasi pemamiriro akagadziridzwa. Compound 4p yakagadzirwa uchishandisa aldehyde substrate yakabatana nebenzonitrile group, inova substrate inobatsira pakugadzirira (4q-4r) supramolecules56. Kuti tiratidze kushanda kwenzira iyi, kugadzirira benzoxazole molecules ine β-lactam moieties (4q-4r) kwakaratidzwa pasi pemamiriro akagadziridzwa kuburikidza nekuita kwealdehyde-functionalized β-lactams, catechol, uye ammonium acetate. Kuedza uku kunoratidza kuti nzira itsva yekugadzira inogona kushandiswa pakushanda kwemamorekuru akaomarara padanho rekupedzisira.
Kuti tiratidze kuti nzira iyi inoshanda zvakasiyana-siyana uye inoshivirira mapoka anoshanda, takadzidza ma aromatic aldehydes akasiyana-siyana anosanganisira mapoka anopa ma electron, mapoka anobvisa ma electron, ma heterocyclic compounds, uye polycyclic aromatic hydrocarbons (Mufananidzo 4, 4s–4aag). Semuenzaniso, benzaldehyde yakashandurwa kuita chigadzirwa chaidiwa (4s) mu 92% yega yega. Ma aromatic aldehydes ane mapoka anopa ma electron (anosanganisira -Me, isopropyl, tert-butyl, hydroxyl, uye para-SMe) akashandurwa zvinobudirira kuita zvigadzirwa zvinoenderana mu goho rakanaka (4t–4x). Ma aldehyde akavharirwa sterically anogona kugadzira zvigadzirwa zve benzoxazole (4y–4aa, 4al) mu goho rakanaka kusvika rakanaka. Kushandiswa kwe meta-substituted benzaldehydes (4ab, 4ai, 4am) kwakabvumira kugadzirwa kwezvigadzirwa zve benzoxazole mu goho rakakura. Ma halogenated aldehydes akadai se (-F, -CF3, -Cl naBr) akapa benzoxazoles dzinoenderana (4af, 4ag na 4ai-4an) muzvibereko zvinogutsa. MaAldehydes ane mapoka ekudhonza maerekitironi (semuenzaniso -CN naNO2) akaitawo zvakanaka uye akapa zvigadzirwa zvaidiwa (4ah na4ao) muzvibereko zvepamusoro.
Rudzi rwekuita runoshandiswa pakugadzira aldehydes a na b. a Mamiriro ekuita: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) uye ZrCl4 (5 mol%) zvakagadziriswa muEtOH (3 mL) pa60 °C kwemaawa matanhatu. b Goho rinoenderana nechinhu chakaparadzaniswa.
Mapolycyclic aromatic aldehydes akadai se1-naphthaldehyde, anthracene-9-carboxaldehyde uye phenanthrene-9-carboxaldehyde anogona kugadzira zvigadzirwa zvinodiwa zve4ap-4ar muzvibereko zvakawanda. Marudzi akasiyana-siyana eheterocyclic aromatic aldehydes anosanganisira pyrrole, indole, pyridine, furan uye thiophene aikwanisa kutsungirira mamiriro ezvinhu ekuita zvakanaka uye aigona kugadzira zvigadzirwa zvinoenderana (4as-4az) muzvibereko zvakawanda. Benzoxazole 4aag yakawanikwa muzvibereko zve52% uchishandisa aliphatic aldehyde inoenderana.
Nzvimbo yemhinduro inoshandisa aldehydes dzekutengesa a, b. a Mamiriro emhinduro: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) uye ZrCl4 (5 mol %) zvakagadziriswa muEtOH (5 mL) pa60 °C kwemaawa mana. b Mugove wacho unoenderana nechinhu chakaparadzaniswa. c Mhinduro yacho yakaitwa pa80 °C kwemaawa matanhatu; d Mhinduro yacho yakaitwa pa100 °C kwemaawa makumi maviri nemana.
Kuti tiwedzere kuratidza kushanda kwakawanda uye kushanda kwenzira iyi, takaedzawo macatechol akasiyana-siyana akatsiviwa. Macatechol akatsiviwa nemono akadai se4-tert-butylbenzene-1,2-diol uye 3-methoxybenzene-1,2-diol akaita zvakanaka neprotocol iyi, zvichiita kuti benzoxazoles 4aaa–4aac ive ne89%, 86%, uye 57% goho, zvichiteerana. Mamwe mabenzoxazoles akatsiviwa nepolysubstituted akagadzirwawo zvinobudirira achishandisa macatechol akatsiviwa nepolysubstituted anoenderana nawo (4aad–4aaf). Hapana zvigadzirwa zvakawanikwa apo macatechol akatsiviwa asina maerekitironi akadai se4-nitrobenzene-1,2-diol uye 3,4,5,6-tetrabromobenzene-1,2-diol akashandiswa (4aah–4aai).
Kugadzirwa kwebenzoxazole muhuwandu hwemagiramu kwakabudirira pasi pemamiriro ezvinhu akagadziriswa, uye compound 4f yakagadzirwa mu85% yezvibereko zvakaparadzana (Mufananidzo 5).
Kugadzirwa kwebenzoxazole 4f muchiyero chegiramu. Mamiriro ekuita: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) uye ZrCl4 (5 mol%) zvakabatwa muEtOH (25 mL) pa60 °C kwemaawa mana.
Zvichibva padata remabhuku, nzira inonzwisisika yekuita nayo zvinhu yakapihwa yekugadzira benzoxazoles kubva ku catechol, aldehyde, uye ammonium acetate pamberi peZrCl4 catalyst (Mufananidzo 6). Catechol inogona chelate zirconium nekubatanidza mapoka maviri ehydroxyl kuti aumbe core yekutanga ye catalytic cycle (I)51. Muchiitiko ichi, semiquinone moiety (II) inogona kuumbwa kuburikidza ne enol-keto tautomerization mu complex I58. Boka re carbonyl rakaumbwa mu intermediate (II) rinoita serinopindirana ne ammonium acetate kuti riumbe intermediate imine (III) 47. Imwe mukana ndeyekuti imine (III^), yakaumbwa ne reaction ye aldehyde ne ammonium acetate, inopindirana ne carbonyl group kuti iumbe intermediate imine-phenol (IV) 59,60. Zvadaro, intermediate (V) inogona kupinda intramolecular cyclization40. Pakupedzisira, pakati peV inosanganiswa neokisijeni yemumhepo, zvichiburitsa chigadzirwa chinodiwa 4 uye zvinoburitsa zirconium complex kuti itange kutenderera kunotevera 61,62.
Zvese zvinogadziriswa nezvinonyungudutsa zvakatengwa kubva kunzvimbo dzekutengeserana. Zvigadzirwa zvese zvinozivikanwa zvakaonekwa nekuenzanisa nedata respectral uye nzvimbo dzekunyungudutsa dzesampuli dzakaedzwa. 1H NMR (400 MHz) uye 13C NMR (100 MHz) spectra dzakanyorwa pachishandiso cheBrucker Avance DRX. Nzvimbo dzekunyungudutsa dzakaonekwa pachishandiso cheBüchi B-545 mucapillary yakavhurika. Zvese zvaiitwa zvakatariswa ne thin-layer chromatography (TLC) uchishandisa silica gel plates (Silica gel 60 F254, Merck Chemical Company). Kuongororwa kweelemental kwakaitwa paPerkinElmer 240-B Microanalyzer.
Mhinduro ye catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) uye ZrCl4 (5 mol %) mu ethanol (3.0 mL) yakasanganiswa zvakatevedzana muchubhu yakavhurika mubhavhu remafuta pa60 °C pasi pemhepo kwenguva yaidiwa. Kufambira mberi kwekuita kwacho kwakatariswa ne thin layer chromatography (TLC). Mushure mekupedza kuita, musanganiswa wakabuda wakatonhodzwa kusvika patembiricha yemukamuri uye ethanol yakabviswa pasi pekumanikidzwa kwakaderera. Musanganiswa wekuita wakasanganiswa ne EtOAc (3 x 5 mL). Zvadaro, zvikamu zvakasanganiswa zve organic zvakaomeswa pamusoro peNa2SO4 isina mvura uye zvakasanganiswa mu vacuo. Pakupedzisira, musanganiswa we crude wakacheneswa ne column chromatography uchishandisa petroleum ether/EtOAc senzira yekuwana pure benzoxazole 4.
Muchidimbu, takagadzira nzira itsva, yakapfava uye yakasvibira yekugadzira benzoxazoles kuburikidza nekuumbwa kweCN neCO bonds mushure me zirconium catalyst. Pasi pemamiriro ekugadzirisa akagadziridzwa, mabenzoxazoles 59 akasiyana akagadzirwa. Mamiriro ekuita anoenderana nemapoka akasiyana-siyana anoshanda, uye ma cores akawanda anoshanda akagadzirwa zvinobudirira, zvichiratidza kugona kwawo kukuru kwekushanda kunotevera. Nokudaro, takagadzira nzira inoshanda, iri nyore uye inoshanda yekugadzira huwandu hwakakura hwezvinhu zvakasiyana-siyana zvebenzoxazole kubva kuma catechol echisikigo pasi pemamiriro egirinhi tichishandisa ma catalysts anodhura zvishoma.
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