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Nnyocha a na-akọ na usoro dị irè nke ukwuu maka imepụta benzoxazoles site na iji catechol, aldehyde na ammonium acetate dị ka ihe oriri site na mmeghachi omume njikọ na ethanol na ZrCl4 dị ka ihe na-akpali akpali. Usoro benzoxazoles (ụdị 59) ka usoro a mepụtara nke ọma na mmepụta ruru 97%. Uru ndị ọzọ nke usoro a gụnyere njikọta buru ibu na iji oxygen dị ka ihe na-eme ka oxidizing. Ọnọdụ mmeghachi omume dị nro na-enye ohere ịrụ ọrụ na-esote, nke na-eme ka njikọta nke ihe dị iche iche nwere usoro dị mkpa na bayoloji dị mfe dịka β-lactams na quinoline heterocycles dị mfe.
Mmepe nke ụzọ ọhụrụ nke mmepụta ihe ndị sitere n'okike nke nwere ike imeri oke n'inweta ihe ndị bara uru ma mee ka ụdị ha dịkwuo iche iche (iji mepee ebe ọhụrụ enwere ike iji ha) adọtala ọtụtụ mmasị na agụmakwụkwọ na ụlọ ọrụ 1,2. Na mgbakwunye na arụmọrụ dị elu nke usoro ndị a, ịdị mma gburugburu ebe obibi nke ụzọ ndị a na-emepụta ga-abụkwa uru dị ukwuu3,4.
Benzoxazoles bụ otu n'ime ihe ndị dị na heterocyclic nke dọtara mmasị dị ukwuu n'ihi ọrụ ha bara ụba na ihe ndị dị ndụ. A kọwo na ihe ndị dị otú ahụ nwere nje bacteria, neuroprotective, anticancer, antiviral, antibacterial, antifungal, na anti-inflammatory activities5,6,7,8,9,10,11. A na-ejikwa ha nke ọma n'ọtụtụ ọrụ ụlọ ọrụ gụnyere ọgwụ, sensoric, agrochemistry, ligands (maka mgbanwe metal catalysis), na sayensị ihe onwunwe12,13,14,15,16,17. N'ihi ihe pụrụ iche ha nwere na ọtụtụ ihe dị iche iche ha nwere, benzoxazoles aghọwo ihe dị mkpa maka imepụta ọtụtụ ihe ndị dị mgbagwoju anya na organic molecules18,19,20. N'ụzọ na-akpali mmasị, ụfọdụ benzoxazoles bụ ngwaahịa eke dị mkpa na molecules ndị metụtara ọgwụ, dị ka nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 na neosalvianene (Foto 1A)26.
(A) Ihe atụ nke ngwaahịa eke sitere na benzoxazole na ihe ndị na-arụ ọrụ na bioactive. (B) Ụfọdụ isi mmalite eke nke catechols.
A na-ejikarị Catechol eme ihe n'ọtụtụ ebe dịka ọgwụ, ihe ịchọ mma na sayensị ihe onwunwe27,28,29,30,31. A gosikwara na Catechol nwere ihe ndị na-egbochi mkpali na ihe ndị na-akpata ọrịa, na-eme ka ha bụrụ ndị nwere ike ịbụ ndị na-agwọ ọrịa32,33. Ihe onwunwe a emeela ka e jiri ya mee ihe n'ịmepụta ihe ịchọ mma na-egbochi ịka nká na ngwaahịa nlekọta akpụkpọ ahụ34,35,36. Ọzọkwa, egosila na catechols bụ ihe ndị na-ebute ụzọ maka mmepụta organic (Foto 1B)37,38. Ụfọdụ n'ime catechol ndị a dị ọtụtụ n'okike. Ya mere, ojiji ya dị ka ihe eji emepụta ihe ma ọ bụ ihe mmalite maka mmepụta organic nwere ike igosipụta ụkpụrụ kemịkalụ akwụkwọ ndụ akwụkwọ ndụ nke "iji akụrụngwa mmeghari ohuru". Emepụtala ọtụtụ ụzọ dị iche iche iji kwadebe ngwakọta benzoxazole arụ ọrụ7,39. Ọrụ oxidative nke njikọ C(aryl)-OH nke catechols bụ otu n'ime ụzọ kachasị mma na nke ọhụrụ maka njikọta benzoxazoles. Ihe atụ nke ụzọ a esi eme ihe na njikọta benzoxazoles bụ mmeghachi omume nke catechols na amines40,41,42,43,44, na aldehydes45,46,47, na alcohols (ma ọ bụ ethers)48, yana ketones, alkenes na alkynes (Foto 2A)49. N'ọmụmụ ihe a, ejiri mmeghachi omume multicomponent (MCR) n'etiti catechol, aldehyde na ammonium acetate mee ihe maka njikọta nke benzoxazoles (Foto 2B). Ejiri ọnụọgụ catalytic nke ZrCl4 mee mmeghachi omume ahụ na ethanol solvent. Rịba ama na enwere ike iwere ZrCl4 dị ka ihe na-akpali akpali Lewis acid akwụkwọ ndụ akwụkwọ ndụ, ọ bụ ihe na-adịghị egbu egbu [LD50 (ZrCl4, ọnụ maka oke) = 1688 mg kg−1] a naghịkwa ewere ya dị ka ihe na-egbu egbu nke ukwuu50. Ejirila ihe na-akpali akpali Zirconium nke ọma dị ka ihe na-akpali akpali maka njikọta nke ọtụtụ ihe ndị dị ndụ. Ọnụ ego dị ala na nkwụsi ike dị elu ha na mmiri na ikuku oxygen na-eme ka ha bụrụ ihe na-akpali akpali na mmepụta ihe ndị sitere n'okike51.
Iji chọta ọnọdụ mmeghachi omume kwesịrị ekwesị, anyị họọrọ 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a na nnu ammonium 3 dị ka mmeghachi omume nlereanya ma mee mmeghachi omume ahụ n'ihu ụdị Lewis acids dị iche iche (LA), ihe mgbaze dị iche iche na okpomọkụ iji mepụta benzoxazole 4a (Tebụl 1). Ahụghị ngwaahịa ọ bụla na enweghị ihe mkpali (Tebụl 1, ntinye 1). Mgbe nke ahụ gasịrị, anwalere 5 mol% nke ụdị Lewis acids dị iche iche dị ka ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 na MoO3 dị ka ihe na-akpali akpali na ihe mgbaze EtOH ma achọpụtara na ZrCl4 bụ ihe kacha mma (Tebụl 1, ntinye 2–8). Iji melite arụmọrụ, a nwalere ihe mgbaze dị iche iche gụnyere dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) na dimethyl sulfoxide (DMSO). Mkpụrụ nke ihe mgbaze niile a nwalere dị ala karịa nke ethanol (Tebụl 1, ntinye 9–15). Iji isi iyi nitrogen ndị ọzọ (dị ka NH4Cl, NH4CN na (NH4)2SO4) kama ammonium acetate emeghị ka mmepụta mmeghachi omume ka mma (Tebụl 1, ntinye 16–18). Ọmụmụ ihe ndị ọzọ gosiri na okpomọkụ dị n'okpuru na karịa 60 °C emeghị ka mmepụta mmeghachi omume ka mma (Tebụl 1, ntinye 19 na 20). Mgbe agbanwere ibu catalyst ka ọ bụrụ 2 na 10 mol%, ihe a na-enweta bụ 78% na 92%, n'otu n'otu (Tebụl 1, ntinye 21 na 22). Mkpụrụ ahụ belatara mgbe e mere mmeghachi omume ahụ n'okpuru ikuku nitrogen, nke na-egosi na ikuku oxygen nwere ike ịrụ ọrụ dị mkpa na mmeghachi omume ahụ (Tebụl 1, ntinye 23). Ịba ụba nke ammonium acetate emeghị ka nsonaazụ mmeghachi omume ahụ ka mma ma belatakwa mmepụta ahụ (Tebụl 1, ntinye 24 na 25). Na mgbakwunye, a hụghị mmụba ọ bụla na mmepụta mmeghachi omume ahụ ka ọ na-abawanye ọnụọgụ catechol (Tebụl 1, ntinye 26).
Mgbe achọpụtachara ọnọdụ mmeghachi omume kacha mma, a mụrụ ọtụtụ ihe dị iche iche na ojiji nke mmeghachi omume ahụ (Foto nke 3). Ebe ọ bụ na alkynes na alkenes nwere otu ọrụ dị mkpa na njikọta organic ma dịkwa mfe ịgbanwe ha, e jiri alkenes na alkynes (4b–4d, 4f–4g) mepụta ọtụtụ ihe ndị sitere na benzoxazole. Site na iji 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde dị ka aldehyde substrate (4e), mkpụrụ ahụ ruru 90%. Na mgbakwunye, e mepụtara benzoxazoles alkyl halo-substituted na mkpụrụ dị elu, nke enwere ike iji maka njikọ na molekul ndị ọzọ na mmepụta ọzọ (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde na 4-(benzyloxy)benzaldehyde nyere benzoxazoles 4j na 4k kwekọrọ na mmepụta dị elu, n'otu n'otu. Site n'iji usoro a, anyị mepụtara ihe ndị sitere na benzoxazole (4l na 4m) nke nwere quinolone moieties53,54,55. E mepụtara Benzoxazole 4n nke nwere otu alkyne abụọ na 84% nke sitere na benzaldehydes 2,4-substituted. E mepụtara ihe mejupụtara bicyclic 4o nke nwere indole heterocycle nke ọma n'okpuru ọnọdụ kachasị mma. E jiri aldehyde substrate nke ejikọtara na otu benzonitrile mepụta compound 4p, nke bụ ihe bara uru maka nkwadebe nke (4q-4r) supramolecules56. Iji gosipụta ojiji nke usoro a, e gosipụtara nkwadebe nke molekul benzoxazole nwere β-lactam moieties (4q-4r) n'okpuru ọnọdụ kachasị mma site na mmeghachi omume nke aldehyde-functionalized β-lactams, catechol, na ammonium acetate. Nnwale ndị a na-egosi na enwere ike iji usoro mmepụta ọhụrụ emepụtara maka ọrụ nke molekul dị mgbagwoju anya n'oge na-adịghị anya.
Iji gosikwuo na usoro a nwere ike ịdị iche iche ma nwee ndidi nye otu ndị na-arụ ọrụ, anyị mụrụ ọtụtụ aldehydes aromatic dị iche iche gụnyere otu ndị na-enye electron, otu ndị na-ewepụ electron, ihe ndị dị na heterocyclic, na polycyclic aromatic hydrocarbons (Foto 4, 4s–4aag). Dịka ọmụmaatụ, a gbanwere benzaldehyde ka ọ bụrụ ngwaahịa achọrọ (4s) na mkpụrụ 92% dịpụrụ adịpụ. A gbanwere aldehydes na-esi ísì ụtọ nwere otu ndị na-enye electron (gụnyere -Me, isopropyl, tert-butyl, hydroxyl, na para-SMe) ka ọ bụrụ ngwaahịa ndị kwekọrọ na ya na mkpụrụ dị mma (4t–4x). Ihe ndị na-egbochi aldehyde nwere ike imepụta ngwaahịa benzoxazole (4y–4aa, 4al) na mkpụrụ dị mma ruo na nke dị mma. Ojiji nke benzaldehydes meta-substituted (4ab, 4ai, 4am) nyere ohere ịkwadebe ngwaahịa benzoxazole na mkpụrụ dị elu. Aldehydes ndị e ji halogenated mee dịka (-F, -CF3, -Cl na Br) nyere benzoxazoles ndị kwekọrọ na ha (4af, 4ag na 4ai-4an) na-enweta ezigbo uru. Aldehydes nwere otu ndị na-ewepụ elektrọn (dịka ọmụmaatụ -CN na NO2) mekwara nke ọma ma nye ngwaahịa achọrọ (4ah na 4ao) na nnukwu uru.
Usoro mmeghachi omume ejiri mee ihe maka njikọta nke aldehydes a na b. a Ọnọdụ mmeghachi omume: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mol%) ka emere na EtOH (3 mL) na 60 °C maka awa 6. b Mkpụrụ ahụ kwekọrọ na ngwaahịa dịpụrụ adịpụ.
Aldehydes aromatic polycyclic dịka 1-naphthaldehyde, anthracene-9-carboxaldehyde na phenanthrene-9-carboxaldehyde nwere ike imepụta ngwaahịa achọrọ 4ap-4ar na nnukwu mkpụrụ. Ọtụtụ aldehydes aromatic heterocyclic gụnyere pyrrole, indole, pyridine, furan na thiophene na-anagide ọnọdụ mmeghachi omume nke ọma ma nwee ike ịmepụta ngwaahịa ndị kwekọrọ na ya (4as-4az) na nnukwu mkpụrụ. E nwetara Benzoxazole 4aag na 52% mkpụrụ site na iji aliphatic aldehyde kwekọrọ.
Mpaghara mmeghachi omume site na iji aldehydes azụmaahịa a, b. a Ọnọdụ mmeghachi omume: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mol%) ka emere mmeghachi omume na EtOH (5 mL) na 60 °C maka awa 4. b Mkpụrụ ahụ kwekọrọ na ngwaahịa dịpụrụ adịpụ. c Emere mmeghachi omume ahụ na 80 °C maka awa 6; d Emere mmeghachi omume ahụ na 100 °C maka awa 24.
Iji gosikwuo etu usoro a si dị iche iche na etu o si arụ ọrụ, anyị nwalekwara ụdị catechol dị iche iche e tinyere n'ọnọdụ ha. Catechol ndị a na-etinye n'otu ụdị dịka 4-tert-butylbenzene-1,2-diol na 3-methoxybenzene-1,2-diol mere nke ọma na usoro a, na-enye benzoxazoles 4aaa–4aac na 89%, 86%, na 57%, n'otu n'otu. E jikwa catechols ndị a na-etinye n'otu ụdị (4aad–4aaf) mepụta ụfọdụ benzoxazoles ndị a na-etinye n'otu ụdị (4aad–4aaf). Enwetaghị ngwaahịa ọ bụla mgbe ejiri catechols ndị a na-etinye n'otu ụdị dịka 4-nitrobenzene-1,2-diol na 3,4,5,6-tetrabromobenzene-1,2-diol (4aah–4aai).
E mechara mmepụta benzoxazole na ọnụọgụ gram nke ọma n'okpuru ọnọdụ kachasị mma, e mekwara ngwakọta 4f na mkpụrụ 85% nke e kewapụrụ iche (Foto 5).
Nhazi nke benzoxazole 4f n'ọkwa gram. Ọnọdụ mmeghachi omume: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) na ZrCl4 (5 mol%) ka emere na EtOH (25 mL) na 60 °C ruo awa anọ.
Dabere na data akwụkwọ, a tụpụtara usoro mmeghachi omume ezi uche dị na ya maka imepụta benzoxazoles site na catechol, aldehyde, na ammonium acetate n'ihu ihe na-akpali akpali ZrCl4 (Foto nke 6). Catechol nwere ike chelate zirconium site na ịhazi otu hydroxyl abụọ iji mepụta isi mbụ nke usoro catalytic (I)51. N'okwu a, enwere ike ịmepụta semiquinone moiety (II) site na enol-keto tautomerization na mgbagwoju anya I58. Otu carbonyl nke e guzobere na etiti (II) yiri ka ọ na-emeghachi omume na ammonium acetate iji mepụta etiti imine (III) 47. Ihe ọzọ nwere ike ime bụ na imine (III^), nke mmeghachi omume nke aldehyde na ammonium acetate mepụtara, na-emeghachi omume na otu carbonyl iji mepụta etiti imine-phenol (IV) 59,60. Mgbe nke ahụ gasịrị, etiti (V) nwere ike ịgafe cyclization intramolecular40. N'ikpeazụ, etiti V na-eme ka ikuku oxygen dị n'etiti, na-enye ngwaahịa achọrọ 4 ma na-ahapụ mgbagwoju zirconium iji malite okirikiri na-esote61,62.
E si n'ebe azụmaahịa zụta ihe ndị na-eme ka ihe dị n'ime mmiri na ihe mgbaze niile. A chọpụtara ngwaahịa niile a maara site na iji ya tụnyere data spectral na ebe agbaze nke ihe atụ ndị a nwalere. E dekọrọ 1H NMR (400 MHz) na 13C NMR (100 MHz) na ngwa Brucker Avance DRX. E kpebiri ebe agbaze na ngwa Büchi B-545 n'ime capillary mepere emepe. E jiri thin-layer chromatography (TLC) nyochaa mmeghachi omume niile site na iji efere silica gel (Silica gel 60 F254, Merck Chemical Company). E mere nyocha elemental na PerkinElmer 240-B Microanalyzer.
A gwakọtara ihe ngwọta nke catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) na ZrCl4 (5 mol%) na ethanol (3.0 mL) n'otu oge n'ime tube mepere emepe n'ime bat mmanụ na okpomọkụ 60 °C n'okpuru ikuku maka oge achọrọ. A na-enyocha ọganihu nke mmeghachi omume ahụ site na iji obere chromatography oyi akwa (TLC). Mgbe emechara mmeghachi omume ahụ, a jụrụ ngwakọta ahụ ka ọ dị jụụ ruo okpomọkụ ụlọ ma wepụ ethanol n'okpuru nrụgide dị ala. A gwakọtara ngwakọta mmeghachi omume ahụ na EtOAc (3 x 5 mL). Mgbe ahụ, a kpọrọ nkụ oyi akwa organic ndị a gwakọtara n'elu Na2SO4 anhydrous ma tinye ha na vacuo. N'ikpeazụ, e jiri kọlụm chromatography mee ka ngwakọta ahụ dị ọcha site na iji petroleum ether/EtOAc dị ka ihe dị elu iji nweta benzoxazole 4 dị ọcha.
Na nchịkọta, anyị emepụtala usoro ọhụrụ, dị nro ma dị ndụ maka imepụta benzoxazoles site na nhazi usoro nke njikọ CN na CO n'ihu ihe na-akpali akpali zirconium. N'okpuru ọnọdụ mmeghachi omume kachasị mma, e mepụtara benzoxazoles 59 dị iche iche. Ọnọdụ mmeghachi omume ahụ dakọtara na otu ọrụ dị iche iche, e mekwara ọtụtụ isi bioactive nke ọma, na-egosi ike ha dị elu maka ịrụ ọrụ na-esote. Ya mere, anyị emepụtala atụmatụ dị irè, dị mfe ma bara uru maka mmepụta buru ibu nke ụdị benzoxazole dị iche iche sitere na catechols eke n'okpuru ọnọdụ akwụkwọ ndụ akwụkwọ ndụ site na iji ihe na-akpali akpali dị ọnụ ala.
A na-etinye data niile e nwetara ma ọ bụ nyochaa n'oge ọmụmụ ihe a n'isiokwu a ebipụtara na faịlụ Ozi Mgbakwunye ya.
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