Darbo tikslas – ištirti heterociklinių junginių, gretimose padėtyse turinčių etinil– ir formilfragmentus, ciklizacijos reakcijas su įvairiais nukleofiliniais reagentais. Darbo metu buvo rastas naujas ir efektyvus pirido[4,3–d]pirimidinų sintezės būdas kurio esmė yra 4–ariletinil–5–pirimidinkarbaldehidų terminė ar mikrobangų inicijuojama reakcija su tret–butilaminu. Parodyta, kad 2–alkinilchinolin–3–karbaldehidai dalyvauja trikomponentinėse reakcijose su pirmininiais aminais ir C– bei P-pronukleofilais sudarydami 1,2–dihidrobenzo[b][1,6]naftiridinus. Pasiūlytas naujas, universalus ir efektyvus būdas benzanuliuotoms sistemoms sintetinti panaudojant metilmerkaptoacetato kalio druską metanolyje. Rasti regioselektyvūs 5,7–dihidrofuro[3,4–d]pirimidinų, 5(H)–pirano[4,3–d]pirimidinų, 1,3–dihidrofuro[3,4–b]chinolinų ir 1H–pirano[4,3–b]chinolinų sintezės būdai tandeminių 5–egzo–dig ir 6–endo–dig ciklizacijos reakcijų pagalba. Rastas efektyvus būdas 2–(2–aril(alkil)–2–oksoetil)–1H–indol–3–karbaldehidams sintetinti iš 2–alkinil–1H–indol–3–karbaldehidų ir metanolio katalizuojant sidabro druskoms. Parodyta, kad 2–alkinilchinolin–3–karbaldehidai reaguodami su dimetilfosfitu bazinėje terpėje sudaro prisijungimo produktus dimetilhidroksi– (2–pakeistus-chinolin–3–il)metilfosfonatus. Pastarieji, esant bazės pertekliaus, persigrupuoja į atitinkamus dimetil–(2–pakeistus-chinolin–3–il)metilfosfatus. Nustatyta, kad 2–(2–piridinil)etinilchinolin–3–karbaldehidas ir 6–ariletinilpirimidin–... [toliau žr. visą tekstą] / The main aims of this investigation were to investigate cyclization reactions of electron–deficient 6–alkynylpyrimidine–5–carbaldehydes and 2–alkynylquinoline–3–carbaldehydes, and electron–rich 2–alkynylindole–3–carbaldehydes and 2–alkynylthiophene–3–carbaldehydes with N–, S–. O–, C– and P–nucleophiles. It was found, that 6–arylethinylpyrimidine–5–carbaldehydes under the treatment with tert–butylamine underwent thermal or microwave–induced cyclization reaction to form pyrido[4,3–d]pyrimidines. A novel and fast synthetic method for preparation of 1,2,3–trisubstituted 1,2–dihydrobenzo[b][1,6]naphthyridines by means of a three–component reaction between 2–alkynylquinoline–3–carbaldehydes, primary amines and C– or P–pronucleophiles was developed. It was showed, that methyl mercaptoacetate was able to trigger a novel benzannulation reaction of the starting materials. Novel, concise and regioselective synthetic methods of 5,7–dihydrofuro[3,4–d]pyrimidine, 5H–pyrano[4,3–d]pyrimidine, 1,3–dihydrofuro[3,4–b]quinolines and 1H–pyrano[4,3–b]quinolines frameworks via regioselective acetalisation/cyclization reactions of 2,4–disubstituted 6–phenylethynylpyrimidine–5–carbaldehydes and 2–alkynylquinoline–3–carbaldehydes were developed. A relatively short and efficient synthesis of 2–(2–oxoethyl)–1H–indole–3–carbaldehydes via tandem 6–endo–dig cyclization from 2–alkynylindole–3–carbaldehydes was developed. It was found that 2–alkynylquinoline–3–carbaldehydes react with dimethylphosphite in... [to full text]
| Identifer | oai:union.ndltd.org:LABT_ETD/oai:elaba.lt:LT-eLABa-0001:E.02~2012~D_20121119_130630-96117 |
| Date | 19 November 2012 |
| Creators | Bukšnaitienė, Rita |
| Contributors | BUTKUS, EUGENIJUS, GETAUTIS, VYTAUTAS, MALINAUSKAS, ALBERTAS, MICKEVIČIUS, VYTAUTAS, ŽILINSKAS, ALBINAS, MARTYNAITIS, VYTAS, VAINILAVIČIUS, POVILAS, ČIKOTIENĖ, INGA, Vilnius University |
| Publisher | Lithuanian Academic Libraries Network (LABT), Vilnius University |
| Source Sets | Lithuanian ETD submission system |
| Language | Lithuanian |
| Detected Language | English |
| Type | Doctoral thesis |
| Format | application/pdf |
| Source | http://vddb.laba.lt/obj/LT-eLABa-0001:E.02~2012~D_20121119_130630-96117 |
| Rights | Unrestricted |
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