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Saa nhwehwɛmu yi bɔ amanneɛ sɛ ɔkwan a ɛyɛ adwuma yie a wɔfa so yɛ benzoxazoles a wɔde catechol, aldehyde ne ammonium acetate yɛ aduane denam coupling reaction wɔ ethanol mu a ZrCl4 yɛ catalyst. Wɔnam saa kwan yi so yɛɛ benzoxazoles ahorow (ahorow 59) yiye wɔ aba a ɛkɔ soro kodu 97% mu. Mfaso afoforo a ɛwɔ saa kwan yi so ne sɛ wɔyɛ nneɛma akɛse ne oxygen a wɔde di dwuma sɛ ade a ɛma ɔhyew. Tebea horow a ɛyɛ mmerɛw no ma kwan ma wɔyɛ adwuma akyiri yi, a ɛma ɛyɛ mmerɛw sɛ wɔbɛhyehyɛ nneɛma ahorow a efi mu ba a ɛwɔ nhyehyɛe ahorow a ɛfa abɔde mu te sɛ β-lactams ne quinoline heterocycles.
Akwan foforo a wɔfa so yɛ nneɛma a nkwa wom a ebetumi adi anohyeto ahorow a ɛwɔ nnuru a ɛsom bo kɛse a wobenya mu na ama wɔn ahorow ahorow akɔ soro (de abue mmeae foforo a wobetumi de adi dwuma) atwetwe adwene kɛse wɔ nhomasua ne nnwuma nyinaa mu1,2. Wɔ saa akwan yi a ɛyɛ adwuma yie kɛseɛ akyi no, akwan a wɔreyɛ no a ɛfa nneɛma a atwa yɛn ho ahyia ho no nso bɛyɛ mfasoɔ kɛseɛ3,4.
Benzoxazoles yɛ heterocyclic nnuru kuw bi a wɔatwetwe adwene kɛse esiane wɔn abɔde mu nneɛma a ɛdɔɔso nti. Wɔabɔ amanneɛ sɛ nnuru a ɛtete saa no wɔ tumi a ɛko tia mmoawa, ntini mu ahobammɔ, kokoram, ɔyare mmoawa, ɔyare mmoawa, fungal, ne ɔyare mmoawa5,6,7,8,9,10,11. Wɔde di dwuma kɛse nso wɔ mfiridwuma ahorow mu a nnuruyɛ, sensorics, agrochemistry, ligands (ma transition metal catalysis), ne nneɛma ho nyansahu ka ho12,13,14,15,16,17. Esiane nnuru soronko a ɛwɔ mu ne sɛnea wotumi de yɛ nneɛma pii nti, benzoxazoles abɛyɛ adansi nneɛma a ɛho hia ma abɔde mu nneɛma a ɛyɛ den pii a wɔyɛ18,19,20. Nea ɛyɛ anigye no, benzoxazoles binom yɛ abɔde mu nneɛma a ɛho hia ne molecule ahorow a ɛfa nnuruyɛ ho, te sɛ nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 ne neosalvianene (Mfonini 1A)26.
(A) Nhwɛso ahorow a ɛfa abɔde mu nneɛma a egyina benzoxazole so ne nnuru a ɛma nipadua no yɛ adwuma ho. (B) Abɔde mu nneɛma bi a wonya fi catechols.
Wɔde catechols di dwuma kɛse wɔ nnwuma pii mu te sɛ nnuruyɛ, ahosiesie ne nneɛma ho nyansahu27,28,29,30,31. Wɔakyerɛ nso sɛ catechols wɔ tumi a ɛko tia ɔyare mmoawa ne nea ɛko tia ɔyare mmoawa, na ɛma ɛyɛ nea wobetumi apaw sɛ nnuru a wɔde sa yare32,33. Saa agyapadeɛ yi ama wɔde adi dwuma wɔ nnuru a wɔde yɛ ahosiesie a ɛko tia onyin ne nneɛma a wɔde hwɛ honam ani34,35,36. Bio nso, wɔada no adi sɛ catechols yɛ ade a etu mpɔn a ɛdi kan ma organic synthesis (Mfonini 1B)37,38. Saa katekol ahorow yi bi dɔɔso wɔ abɔde mu. Enti, nea wɔde di dwuma sɛ ade a wɔde yɛ nneɛma anaasɛ ade a wɔde fi ase ma nneɛma a nkwa wom yɛ no betumi ayɛ green chemistry nnyinasosɛm a ɛne sɛ “wɔde nneɛma a wɔyɛ no foforo bedi dwuma” no mu. Wɔayɛ akwan ahodoɔ pii a wɔfa so siesie benzoxazole nnuru a ɛyɛ adwuma7,39. Oxidative functionalization of the C(aryl)-OH bond of catechols yɛ akwan a ɛyɛ anigye na ɛyɛ foforo sen biara a wɔfa so yɛ benzoxazoles no mu biako. Saa kwan yi ho nhwɛsoɔ wɔ benzoxazoles a wɔyɛ mu ne sɛnea catechols ne amines40,41,42,43,44, ne aldehydes45,46,47, ne alcohols (anaasɛ ethers)48, ne ketones, alkenes ne alkynes nso yɛ adwuma (Mfonini 2A)49. Wɔ saa nhwehwɛmu yi mu no, wɔde multicomponent reaction (MCR) a ɛda catechol, aldehyde ne ammonium acetate ntam dii dwuma de yɛɛ benzoxazoles (Mfonini 2B). Wɔde ZrCl4 dodow a ɛyɛ catalytic a ɛwɔ ethanol solvent mu na ɛyɛɛ adeyɛ no. Hyɛ no nsow sɛ wobetumi abu ZrCl4 sɛ Lewis acid a ɛyɛ ahabammono a ɛma nneɛma yɛ kɛse, ɛyɛ aduru a awuduru nnim pii [LD50 (ZrCl4, a wɔnom ma mprako) = 1688 mg kg−1] na wonsusuw sɛ ɛyɛ awuduru kɛse50. Wɔde zirconium catalysts nso adi dwuma yiye sɛ catalysts a wɔde yɛ nneɛma ahorow a ɛwɔ abɔde mu. Wɔn bo a ɛba fam ne sɛnea wotumi gyina pintinn kɛse wɔ nsu ne oxygen ho no ma wɔyɛ nneɛma a ɛhyɛ bɔ wɔ nneɛma a wɔde yɛ nneɛma a nkwa wom mu51.
Sɛnea ɛbɛyɛ a yebehu tebea horow a ɛfata a wɔde yɛ ade no, yɛpaw 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a ne ammonium nkyene 3 sɛ nhwɛsode nneyɛe na yɛyɛɛ nneyɛe no wɔ Lewis acid ahorow (LA), nnuru ahorow a wɔde yɛ nneɛma ne ɔhyew ahorow anim de yɛɛ benzoxazole 4a (Table 1). Wɔanhu ade biara a wɔde yɛ ade bere a na catalyst nni hɔ (Table 1, entry 1). Akyiri yi, wɔsɔɔ Lewis acid ahodoɔ te sɛ ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 ne MoO3 hwɛeɛ sɛ catalysts wɔ EtOH solvent mu na wɔhunuu sɛ ZrCl4 na ɛyɛ papa (Table 1, entries 2–8). Sɛnea ɛbɛyɛ a ɛbɛyɛ adwuma yiye no, wɔsɔɔ nnuru ahorow a wɔde siw ano a dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) ne dimethyl sulfoxide (DMSO) ka ho hwɛe. Na nsuo a ɛfiri nnuru a wɔsɔɔ hwɛeɛ no nyinaa mu baeɛ sene ethanol deɛ (Table 1, entries 9–15). Nitrogen fibea afoforo (te sɛ NH4Cl, NH4CN ne (NH4)2SO4) a wɔde dii dwuma sen ammonium acetate a wɔde dii dwuma no amma adeyɛ no aba ankɔ anim (Table 1, nsɛm a wɔakyerɛw 16–18). Nhwehwɛmu foforo kyerɛe sɛ ɔhyew a ɛba fam ne nea ɛboro 60 °C no amma adeyɛ no aba ankɔ soro (Table 1, nsɛm a wɔakyerɛw 19 ne 20). Bere a wɔsesaa catalyst loading no kɔɔ 2 ne 10 mol % no, aba a wonyae no yɛ 78% ne 92%, sɛnea ɛte biara (Table 1, entries 21 ne 22). Aba no so tew bere a wɔyɛɛ adeyɛ no wɔ nitrogen wim tebea ase no, na ɛkyerɛ sɛ ebia mframa mu oxygen di dwuma titiriw wɔ adeyɛ no mu (Table 1, entry 23). Ammonium acetate dodow a ɛkɔɔ soro no amma nea efii adeyɛ no mu bae no ankɔ anim na mpo ɛmaa aba a wonya no so tew (Table 1, nsɛm a wɔakyerɛw 24 ne 25). Bio nso, wɔanhu nkɔso biara wɔ reaction aba no mu bere a catechol dodow a ɛkɔ soro no (Table 1, entry 26).
Bere a wɔkyerɛɛ tebea horow a eye sen biara a wɔde yɛ ade akyi no, wɔyɛɛ sɛnea adeyɛ no tumi yɛ adwuma wɔ mmeae pii ne sɛnea wɔde di dwuma no ho nhwehwɛmu (Mfonini 3). Esiane sɛ alkynes ne alkenes wɔ dwumadi akuw a ɛho hia wɔ organic synthesis mu na ɛnyɛ den sɛ wobegye atom sɛ wɔbɛkɔ so derivatization nti, wɔde alkenes ne alkynes (4b–4d, 4f–4g) yɛɛ benzoxazole derivatives pii. Sɛ wɔde 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde dii dwuma sɛ aldehyde substrate (4e) a, aba no duu 90%. Afei nso, wɔyɛɛ benzoxazoles a wɔde alkyl halo asi ananmu wɔ aba a ɛkɔ soro mu, a wobetumi de adi dwuma ama ligation ne molecule afoforo ne derivatization foforo (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde ne 4-(benzyloxy)benzaldehyde maa benzoxazoles a ɛne no hyia 4j ne 4k wɔ soro aba, sɛnea ɛte biara. Yɛde saa kwan yi dii dwuma no, yetumi yɛɛ benzoxazole a efi mu ba (4l ne 4m) a quinolone afã horow53,54,55 wom. Wɔyɛɛ Benzoxazole 4n a alkyne akuw abien wom wɔ 84% aba mu fii benzaldehydes 2,4 a wɔde asi ananmu mu. Wɔyɛɛ bicyclic compound 4o a indole heterocycle wom no yiye wɔ tebea horow a eye sen biara mu. Wɔde aldehyde substrate a ɛbata benzonitrile kuw bi ho na ɛyɛɛ compound 4p, a ɛyɛ substrate a mfaso wɔ so ma (4q-4r) supramolecules56. Sɛnea ɛbɛyɛ na wɔasi sɛnea wɔde saa kwan yi di dwuma so dua no, wɔdaa benzoxazole molecules a β-lactam afã horow (4q–4r) wom a wosiesiee adi wɔ tebea horow a eye sen biara mu denam aldehyde-functionalized β-lactams, catechol, ne ammonium acetate a wɔde yɛ adwuma no so. Saa nhwehwɛmu ahorow yi kyerɛ sɛ wobetumi de ɔkwan foforo a wɔayɛ a wɔfa so yɛ nneɛma no adi dwuma de ayɛ molecule ahorow a ɛyɛ den no dwumadi wɔ akyiri yi.
Sɛnea ɛbɛyɛ a yɛbɛkɔ so akyerɛ sɛnea saa kwan yi tumi yɛ adwuma pii na ɛma akuw a wɔyɛ adwuma no gyina ano no, yesuaa aldehydes ahorow ahorow a ɛyɛ huam a akuw a wɔde ɛlɛtrɔnik ma, akuw a wɔtwe ɛlɛtrɔnik, heterocyclic nnuru, ne polycyclic aromatic hydrocarbons ka ho (Mfonini 4, 4s–4aag). Sɛ nhwɛso no, wɔdanee benzaldehyde yɛɛ no ​​ade a wɔpɛ (4s) wɔ 92% a wɔatew wɔn ho mu. Wɔdanee aldehyde a ɛyɛ huam a ɛwɔ akuw a ɛma ɛlɛtrɔnik (a -Me, isopropyl, tert-butyl, hydroxyl, ne para-SMe ka ho) no yiye ma ɛbɛyɛɛ nneɛma a ɛne no hyia wɔ aba a eye kyɛn so (4t–4x). Sterically hindered aldehyde substrates betumi ama benzoxazole nneɛma (4y–4aa, 4al) aba pa kosi papa. Meta-substituted benzaldehydes (4ab, 4ai, 4am) a wɔde dii dwuma no maa kwan ma wɔyɛɛ benzoxazole nneɛma wɔ aba pii mu. Halogenated aldehydes te sɛ (-F, -CF3, -Cl ne Br) maa benzoxazoles a ɛne no hyia (4af, 4ag ne 4ai-4an) wɔ aba a ɛma abotɔyam. Aldehydes a ɛwɔ akuw a ɛtwe ɛlɛtrɔnik (sɛ nhwɛso no -CN ne NO2) nso yɛɛ adwuma yiye na ɛmaa nneɛma a wɔpɛ (4ah ne 4ao) wɔ aba a ɛkɔ soro mu.
Reaction series a wɔde yɛ aldehydes a ne b. a Nneyɛe tebea: Wɔde 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) ne ZrCl4 (5 mol%) yɛɛ adwuma wɔ EtOH (3 mL) mu wɔ 60 °C mu nnɔnhwerew 6. b Aba a wonya no ne ade a wɔatew wɔn ho no hyia.
Polycyclic aromatic aldehydes te sɛ 1-naphthaldehyde, anthracene-9-carboxaldehyde ne phenanthrene-9-carboxaldehyde betumi ama wɔanya nneɛma a wɔpɛ 4ap-4ar wɔ aba pii mu. Heterocyclic aromatic aldehydes ahodoɔ a pyrrole, indole, pyridine, furan ne thiophene ka ho no gyinaa tebea a ɛyɛ adwuma no ano yie na ɛtumi yɛɛ nneɛma a ɛne no hyia (4as-4az) wɔ aba kɛseɛ mu. Wɔde aliphatic aldehyde a ɛne no hyia no nyaa Benzoxazole 4aag wɔ 52% aba mu.
Reaction region a wɔde aldehydes a wɔtɔn di dwuma a, b. a Nneyɛe tebea: Wɔde 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) ne ZrCl4 (5 mol %) yɛɛ adwuma wɔ EtOH (5 mL) mu wɔ 60 °C mu h 4. b Aba a wonya no ne ade a wɔatew wɔn ho no hyia. c Wɔyɛɛ adeyɛ no wɔ 80 °C mu h 6; d Wɔyɛɛ adeyɛ no wɔ 100 °C mu 24 h.
Sɛnea ɛbɛyɛ na yɛakyerɛkyerɛ sɛnea saa kwan yi tumi yɛ adwuma wɔ mmeae pii na wɔde di dwuma no mu bio no, yɛsɔɔ catechol ahorow a wɔde asi ananmu nso hwɛe. Monosubstituted catechols te sɛ 4-tert-butylbenzene-1,2-diol ne 3-methoxybenzene-1,2-diol yɛɛ adwuma yiye ne saa protocol yi, maa benzoxazoles 4aaa–4aac wɔ 89%, 86%, ne 57% aba, sɛnea ɛte biara. Wɔde polysubstituted benzoxazoles bi nso yɛɛ yiye denam polysubstituted catechols a ɛne no hyia (4aad–4aaf) so. Wɔannya nneɛma biara bere a wɔde catechols a wɔde asi ananmu a ɛlɛtrɔnik nnim te sɛ 4-nitrobenzene-1,2-diol ne 3,4,5,6-tetrabromobenzene-1,2-diol dii dwuma (4aah–4aai).
Wɔyɛɛ benzoxazole a wɔde gram dodow yɛ no yiye wɔ tebea horow a ɛyɛ papa mu, na wɔyɛɛ aduru 4f wɔ 85% a wɔatew wɔn ho aba mu (Mfonini 5).
Gram-scale a wɔde yɛ benzoxazole 4f. Nneyɛe tebea: Wɔde 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) ne ZrCl4 (5 mol%) yɛɛ adwuma wɔ EtOH (25 mL) mu wɔ 60 °C mu h 4.
Wogyina nhoma mu nsɛm so ahyɛ nyansa sɛ wɔmfa ɔkwan a ntease wom a wɔbɛfa so ayɛ benzoxazoles afi catechol, aldehyde, ne ammonium acetate mu wɔ ZrCl4 catalyst anim (Mfonini 6). Catechol tumi chelate zirconium denam hydroxyl akuw abien a ɛka bom ma ɛyɛ catalytic cycle (I)51 no mu ade titiriw a edi kan no so. Wɔ eyi mu no, wobetumi afa enol-keto tautomerization so ayɛ semiquinone fã (II) no wɔ complex I58 mu. Ɛda adi sɛ carbonyl kuw a wɔayɛ wɔ mfinimfini (II) mu no ne ammonium acetate yɛ adwuma ma ɛyɛ mfinimfini imine (III) 47. Ade foforo a ebetumi aba ne sɛ imine (III^), a ɛnam aldehyde ne ammonium acetate a ɛyɛ adwuma so na ɛbae no ne carbonyl kuw no yɛ adwuma ma ɛyɛ mfinimfini imine-phenol (IV) 59, Akyiri yi, mfinimfini (V) betumi afa intramolecular cyclization40 mu. Awiei koraa no, wɔde wim oxygen yɛ oxidized V a ɛwɔ ntam no, na ɛma wonya ade a wɔpɛ 4 na ɛma zirconium complex no fi ase de fi kyinhyia a edi hɔ no ase61,62.
Wɔtɔɔ reagents ne solvents nyinaa fii aguadidan ahorow mu. Wɔde spectral data ne melting points a wɔde totoo nhwɛsode a wɔasɔ ahwɛ no ho na ɛkyerɛɛ nneɛma a wonim nyinaa. Wɔkyerɛw 1H NMR (400 MHz) ne 13C NMR (100 MHz) spectra wɔ Brucker Avance DRX adwinnade so. Wɔde Büchi B-545 afiri bi a ɛwɔ ntini a ɛbue mu na ɛkyerɛɛ mmeae a ɛbɛbɔ. Wɔnam thin-layer chromatography (TLC) a wɔde silica gel mprɛte (Silica gel 60 F254, Merck Chemical Company) dii dwuma so hwɛɛ nneyɛe nyinaa. Wɔde PerkinElmer 240-B Microanalyzer yɛɛ elemental nhwehwɛmu.
Wɔde catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) ne ZrCl4 (5 mol %) a wɔde ahyɛ ethanol (3.0 mL) mu afra mu nnidiso nnidiso wɔ afiri a wɔabue mu wɔ ngo aguaree mu wɔ 60 °C wɔ mframa ase bere a wɔhwehwɛ. Wɔde thin layer chromatography (TLC) hwɛɛ sɛnea adeyɛ no rekɔ so. Bere a wɔyɛɛ ade no wiei no, wɔmaa afrafrade a efii mu bae no yɛɛ nwini koduu dan mu hyew mu na woyii ethanol fii mu wɔ nhyɛso a wɔatew so mu. Wɔde EtOAc (3 x 5 mL) guu afrafrade a wɔde yɛ ade no mu. Afei, wɔde Na2SO4 a nsu nnim so wee organic layers a wɔaka abom no na wɔde guu vacuum mu. Awiei koraa no, wɔde column chromatography tew afrafrade a wɔmfa nhyehyɛ mu no ho de petroleum ether/EtOAc dii dwuma sɛ eluent ma wonya benzoxazole 4 a ɛho tew.
Sɛ yɛbɛbɔ no mua a, yɛayɛ nhyehyɛe foforo, a ɛyɛ mmerɛw na ɛyɛ ahabammono a wɔde bɛyɛ benzoxazoles denam CN ne CO nkitahodi a wɔhyehyɛ nnidiso nnidiso wɔ zirconium catalyst anim. Wɔ tebea horow a wɔayɛ no yiye no ase no, wɔyɛɛ benzoxazoles ahorow 59. Nneyɛe tebea horow no ne dwumadi akuw ahorow hyia, na wɔyɛɛ bioactive cores pii yiye, a ɛkyerɛ sɛ tumi kɛse a ɛwɔ hɔ ma dwumadi a edi hɔ. Enti, yɛayɛ ɔkwan a etu mpɔn, ɛnyɛ den na mfaso wɔ so a yɛde bɛyɛ benzoxazole a wonya fi abɔde mu catechols mu kɛse wɔ tebea horow a ɛyɛ ahabammono mu denam nneɛma a ɛma nneɛma yɛ kɛse a ne bo nyɛ den so.
Wɔde nsɛm a wonyae anaa wɔhwehwɛɛ mu wɔ adesua yi mu nyinaa ka asɛm a wɔatintim yi ne ne Supplementary Information fael ahorow no ho.
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