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He zirchianna hian benzoxazoles siamna atana hmanraw tha tak a report a, catechol, aldehyde leh ammonium acetate te chu feedstock atan hmangin ethanol-a coupling reaction hmangin ZrCl4 chu catalyst atan a hmang a ni. Hetiang hmang hian benzoxazoles series (chi 59) chu hlawhtling takin siam chhuah a ni a, yield 97% thleng a ni. Hetiang approach hian a thatna dangte chu large-scale synthesis leh oxygen chu oxidizing agent atana hman te hi a ni. Mild reaction conditions hian a hnu lama functionalization a phalsak a, hei hian biologically relevant structure β-lactams leh quinoline heterocycles te nei derivative hrang hrang siamna a ti awlsam hle.
Compound man to tak tak hmuh theihna tura tihkhawtlai awmte hneh thei tur leh an chi hrang hrang tihpun theihna tur (application area thar hawn theihna tur) organic synthesis hmanraw thar siam chhuah hian zirna leh industry-ah ngaihven a hlawh hle Heng hmanrua te hi a tangkai em em bakah hian, kalphung siam mekte hian boruak tichhe lo a nih avangin hlawkna nasa tak a thlen bawk ang3,4.
Benzoxazoles hi heterocyclic compound class pakhat a ni a, biological activity hautak tak a neih avangin ngaihven a hlawh hle. Chutiang compound te hian antimicrobial, neuroprotective, anticancer, antiviral, antibacterial, antifungal, leh anti-inflammatory activity an nei tih an sawi5,6,7,8,9,10,11. Industrial field hrang hrangah pawh an hmang nasa hle a, chung zingah chuan damdawi lam, sensorics, agrochemistry, ligand (transition metal catalysis atan), leh materials science te pawh an tel a ni12,13,14,15,16,17. Chemical property danglam bik leh hmanraw tangkai tak an neih avangin benzoxazoles te hi complex organic molecule tam tak siamna atana building block pawimawh tak a lo ni ta a ni18,19,20. Ngaihven awm tak chu benzoxazole thenkhat hi natural product pawimawh tak tak leh pharmacologically relevant molecule an ni a, chungte chu nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 leh neosalvianene te an ni (Figure 1A)
(A) Benzoxazole hmanga siam thilsiam leh bioactive compound entirnan. (B) Catechols awmna natural source thenkhat.
Catechol hi damdawi lam, cosmetics leh materials science-ah te hman a ni nasa hle27,28,29,30,31. Catechols hian antioxidant leh anti-inflammatory property a nei tih hmuhchhuah a ni bawk a, hei vang hian therapeutic agents atana candidate ni thei tur a ni32,33. He property hian anti-aging cosmetics leh skin care products siamnaah a hmang nasa hle a ni34,35,36. Chubakah, catechols te hi organic synthesis atana precursor tha tak an nih thu hmuhchhuah a ni bawk (Figure 1B)37,38. Heng catechol thenkhat hi nature-ah hian a tam hle. Chuvangin, organic synthesis atana raw material emaw starting material emaw atana hman hian green chemistry principle “utilizing renewable resources” chu a keng tel thei a ni. Functionalized benzoxazole compound siamna tur kawng hrang hrang siam a ni tawh7,39. Catechols C(aryl)-OH bond oxidative functionalization hi benzoxazoles siamna atana hmanraw ngaihnawm leh thar ber pakhat a ni. Benzoxazoles siamna atana hetiang approach entir nan hian catechols te chu amines40,41,42,43,44 te, aldehydes te45,46,47 te, alcohols (or ethers)48 te, chubakah ketones, alkenes leh alkynes te nena an inrem dan te hi a ni (Figure 2A)49. He zirchiannaah hian benzoxazoles siamna atan hian catechol, aldehyde leh ammonium acetate inkara multicomponent reaction (MCR) hman a ni (Figure 2B). Reaction hi ethanol solvent-a ZrCl4 catalytic amount hmangin an ti a. ZrCl4 hi green Lewis acid catalyst anga ngaih theih a ni tih hre reng ang che, compound toxic lo zawk [LD50 (ZrCl4, oral for rats) = 1688 mg kg−1] a ni a, toxic sang takah ngaih a ni lo50. Zirconium catalyst hi organic compound hrang hrang siamna atana catalyst atan pawh hlawhtling takin an hmang tawh bawk. An man tlawm leh tui leh oxygen laka an stability sang avangin organic synthesis-a catalyst beisei awm tak an ni51.
Reaction condition tha tak zawng turin model reaction atan 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a leh ammonium salt 3 te kan thlang a, Lewis acid hrang hrang (LA), solvent hrang hrang leh temperature hrang hrang awmnaah benzoxazole 4a siam turin kan ti a (Table 1). Catalyst awm lohnaah chuan product hmuh tur a awm lo (Table 1, entry 1). Chumi hnuah Lewis acid hrang hrang ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 leh MoO3 te chu EtOH solvent-ah catalyst atan 5 mol % test a ni a, ZrCl4 chu a tha ber tih hmuhchhuah a ni (Table 1, entries 2–8). Efficiency tihsan nan solvent hrang hrang test a ni a, chung zingah chuan dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) leh dimethyl sulfoxide (DMSO) te pawh an tel. Solvent test zawng zawngte yield chu ethanol aiin a hniam zawk (Table 1, entry 9–15). Ammonium acetate aiah nitrogen source dang (NH4Cl, NH4CN leh (NH4)2SO4 ang chi) hman chuan reaction yield a ti tha lo (Table 1, entry 16–18). Zirna dang neih belh leh chuan 60 °C hnuai leh a chunglam temperature chuan reaction yield a tisang lo tih hmuhchhuah a ni (Table 1, entry 19 leh 20). Catalyst loading chu 2 leh 10 mol %-a thlak a nih chuan yield chu 78% leh 92% a ni (Table 1, entry 21 leh 22). Nitrogen boruak hnuaia reaction an tih chuan yield a tlahniam a, hei hian boruak oxygen hian reaction-ah hian hmun pawimawh tak a chang thei tih a tilang (Table 1, entry 23). Ammonium acetate tihpun hian reaction result a ti tha lo va, yield pawh a ti tlem hle (Table 1, entry 24 leh 25). Chu bakah, catechol tam lutuk chuan reaction yield-ah hmasawnna a awm lo (Table 1, entry 26).
Reaction condition tha ber an hriat hnuah, reaction versatility leh applicability te chu zirchian a ni (Figure 3). Alkynes leh alkenes te hian organic synthesis-ah functional group pawimawh tak tak an nei a, derivatization tihpunna atana awlsam taka an hman theih avangin benzoxazole derivative engemaw zat chu alkenes leh alkynes (4b–4d, 4f–4g) hmangin an siam chhuak a ni. Aldehyde substrate (4e) atan 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde hman chuan 90% a tling a ni. Chu bakah, alkyl halo-substituted benzoxazoles chu yield sang takah siam a ni a, chu chu molecule dang nena ligation leh further derivatization atan hman theih a ni (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde leh 4-(benzyloxy)benzaldehyde te hian a inmil benzoxazoles 4j leh 4k in high a pe a ni yields, a hnuaia mi ang hian a ni. Hetiang hmang hian quinolone moieties53,54,55 awmna benzoxazole derivatives (4l leh 4m) hlawhtling takin kan siam chhuak a. Alkyne group pahnih awmna Benzoxazole 4n chu 2,4-substituted benzaldehydes atanga 84% yield-in siam a ni. Indole heterocycle awmna bicyclic compound 4o chu optimized condition hnuaiah hlawhtling takin an siam chhuak a. Compound 4p hi benzonitrile group-a inzawm aldehyde substrate hmanga siam a ni a, hei hi (4q-4r) supramolecules siamna atana substrate tangkai tak a ni Hetiang hmanraw hman tangkai theihna tur hian benzoxazole molecule β-lactam moieties (4q–4r) awmna siam chu aldehyde-functionalized β-lactams, catechol, leh ammonium acetate te reaction hmangin optimized condition hnuaiah entir a ni. Heng experiment te hian synthetic approach siam thar hi complex molecule te late-stage functionalization atan hman theih a nih thu a tarlang a ni.
Hetiang method hi functional group-a versatility leh tolerance tihlan belh zel nan aromatic aldehyde hrang hrang kan zirchiang a, chung zingah chuan electron-donating group, electron-withdrawing group, heterocyclic compound, leh polycyclic aromatic hydrocarbons te pawh an tel a ni (Figure 4, 4s–4aag). Entirnan, benzaldehyde chu 92% isolated yield-ah duhthusam (4s)-ah an chantir a. Electron-donating group (-Me, isopropyl, tert-butyl, hydroxyl, leh para-SMe te pawh tel) nei aromatic aldehyde te chu hlawhtling takin a inmil tur product-ah yield tha tak (4t–4x)-ah an chantir a. Sterically hindered aldehyde substrate hian benzoxazole products (4y–4aa, 4al) a siam chhuak thei a, yield tha tak atanga tha tak thlengin a siam thei a ni. Meta-substituted benzaldehydes (4ab, 4ai, 4am) hman a nih avangin benzoxazole products chu yield sang takin siam theih a ni. Halogenated aldehyde (-F, -CF3, -Cl leh Br) te chuan a inmil tur benzoxazoles (4af, 4ag leh 4ai-4an) te chu a hlawhtling hle. Electron withdrawing group (eg -CN leh NO2) nei aldehyde te pawhin an inrem tha hle a, duhthusam (4ah leh 4ao) te chu yield sang takin an pe chhuak bawk.
Aldehyde a leh b siamna atana hman thin reaction series. a Reaction conditions: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) leh ZrCl4 (5 mol%) te chu EtOH (3 mL) ah 60 °C ah 6 h chhung an reacted a. b Yield chu isolated product nen a inmil a ni.
Polycyclic aromatic aldehyde 1-naphthaldehyde, anthracene-9-carboxaldehyde leh phenanthrene-9-carboxaldehyde te hian duhthusam 4ap-4ar chu yield sang takin a siam thei a ni. Heterocyclic aromatic aldehyde hrang hrang pyrrole, indole, pyridine, furan leh thiophene te chuan reaction condition te chu an tuar tha hle a, a inmil tur product (4as-4az) chu yield sang takah an siam thei a ni. Benzoxazole 4aag chu a inmil aliphatic aldehyde hmangin 52% yield-in an hmu a ni.
Commercial aldehyde hmanga reaction region a, b. a Reaction conditions: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) leh ZrCl4 (5 mol %) te chu EtOH (5 mL) ah 60 °C ah 4 h chhung an reacted a. b Yield chu isolated product nen a inmil a ni. c Reaction chu 80 °C-ah 6 h chhung an ti a; d Reaction chu 100 °C ah 24 h chhung an ti a.
Hetiang method hi a versatility leh applicability tih chiang zawk nan substituted catechols hrang hrang kan test bawk. Monosubstituted catechols 4-tert-butylbenzene-1,2-diol leh 3-methoxybenzene-1,2-diol te chuan he protocol hmang hian an inrem tha hle a, benzoxazoles 4aaa–4aac chu 89%, 86% leh 57% yield-ah an pe chhuak a ni. Polysubstituted benzoxazole thenkhat pawh a inmil polysubstituted catechols (4aad–4aaf) hmangin hlawhtling takin an siam chhuak bawk. Electron tlachham substituted catechols 4-nitrobenzene-1,2-diol leh 3,4,5,6-tetrabromobenzene-1,2-diol te hman a nih chuan product engmah hmuh tur a awm lo (4aah–4aai).
Benzoxazole gram quantity-a siam chu optimized condition-ah hlawhtling takin an ti thei a, compound 4f chu 85% isolated yield-ah siam a ni bawk (Figure 5).
Gram-scale-a benzoxazole siam chhuah 4f. Reaction condition: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) leh ZrCl4 (5 mol%) te chu EtOH (25 mL) ah 60 °C ah 4 h chhung an reacted a.
Literature data atanga chhut chuan ZrCl4 catalyst awmnaah catechol, aldehyde, leh ammonium acetate atanga benzoxazoles siamna tur reaction mechanism dik tak an rawt a (Figure 6). Catechol hian hydroxyl group pahnih inzawmkhawmin zirconium chu a chelate thei a, chu chuan catalytic cycle (I)51-a core hmasa ber a siam thei a ni. Chutiang a nih chuan complex I58-ah enol-keto tautomerization hmangin semiquinone moiety (II) chu siam theih a ni. Intermediate (II)-a carbonyl group lo awm chu ammonium acetate nen an inrem a, intermediate imine (III) a siam niin a lang 47. Thil awm thei dang chu aldehyde leh ammonium acetate inrem avanga siam imine (III^) chuan carbonyl group nen inrem in intermediate imine-phenol (IV) a siam thei a ni 59, Chumi hnuah chuan intermediate (V) chu intramolecular cyclization40 a paltlang thei a ni. A tawpah chuan intermediate V chu atmospheric oxygen nen oxidized a ni a, duhthusam product 4 a lo chhuak a, zirconium complex chu chhuahsanin cycle lo awm tur chu a tan ta a ni61,
Reagent leh solvent zawng zawng hi sumdawnna hmun atanga lei vek a ni. Product hriat zawng zawng chu spectral data leh tested sample-te melting point nena khaikhin a ni. Brucker Avance DRX instrument hmangin 1H NMR (400 MHz) leh 13C NMR (100 MHz) spectra te chu record a ni. Melting points chu Büchi B-545 apparatus hmangin open capillary-ah an chhut a. Reaction zawng zawng chu silica gel plate (Silica gel 60 F254, Merck Chemical Company) hmangin thin-layer chromatography (TLC) hmangin an enfiah vek a ni. Elemental analysis chu PerkinElmer 240-B Microanalyzer hmangin an ti a.
Ethanol (3.0 mL)-a catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) leh ZrCl4 (5 mol %) solution chu oil bath-ah oil bath-ah 60 °C-ah boruak hnuaiah a mamawh hun chhung chu a zawnin a hrual a. Reaction kal zel dan chu thin layer chromatography (TLC) hmangin an enfiah a. Reaction zawh hnuah a chhuak chu room temperature-ah tihlum a ni a, ethanol chu pressure tihhniam hnuaiah lakchhuah a ni. Reaction mixture chu EtOAc (3 x 5 mL) hmangin a diluted a. Tichuan, organic layer inzawmkhawmte chu anhydrous Na2SO4-ah an vawt a, vacuum-ah an concentrate a. A tawpah chuan crude mixture chu column chromatography hmangin petroleum ether/EtOAc chu eluent atan hmangin tihthianghlim a ni a, benzoxazole 4 thianghlim tak a awm ta a ni.
A tawi zawngin, zirconium catalyst awmna hmuna CN leh CO bonds sequential formation hmanga benzoxazoles siamna tur novel, mild leh green protocol kan siam a ni. Optimized reaction condition hnuaiah hian benzoxazole hrang hrang 59 siam a ni. Reaction conditions hi functional group hrang hrang nen a inmil a, bioactive core engemawzat hlawhtling taka siam chhuah a ni a, hei hian a hnu lama functionalization atana an theihna sang tak a tilang a ni. Chuvangin, green condition hnuaia natural catechol atanga benzoxazole derivatives chi hrang hrang lian tham tak, low-cost catalyst hmanga siam chhuah theihna tur strategy tha tak, awlsam leh tangkai tak kan siam ta a ni.
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