Pregled bibliografske jedinice broj: 495907
Regiospecific formation of 9, 3-propeno-8-aza-9H-xanthines and their conversion into 3-(2, 3-dihydroxypropyl)-8-aza-9H-xanthine and derivatives
Regiospecific formation of 9, 3-propeno-8-aza-9H-xanthines and their conversion into 3-(2, 3-dihydroxypropyl)-8-aza-9H-xanthine and derivatives // Journal of the Chemical Society. Perkin Transactions 1, (1989), 4; 757-763 doi:10.1039/P19890000757 (međunarodna recenzija, članak, znanstveni)
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Naslov
Regiospecific formation of 9, 3-propeno-8-aza-9H-xanthines and their conversion into 3-(2, 3-dihydroxypropyl)-8-aza-9H-xanthine and derivatives
Autori
Jokić, Milan ; Škarić, Vinko
Izvornik
Journal of the Chemical Society. Perkin Transactions 1 (1472-7781)
(1989), 4;
757-763
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
3; 9-propano-8-aza-9H-xanthine
Sažetak
A novel series of C-11 -functionalized 3, 9-propano-8-aza-9H-xanthine and related compounds have been synthesized. With 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU), 11-methylsulphonyloxy-3, 9-propano-8-aza-9H-xanthine (11) underwent a regiospecific elimination to give 9, 3-propeno-8-aza-9H-xanthine (19). An equally interesting result was obtained from (19) on osmium tetraoxide oxidation, when 10, 11-dihydroxy-3, 9-propano-8-aza-9H-xanthine (20) was formed and then transformed into 3-(2, 3-dihydroxypropyl)-8-aza-9H-xanthine (22) by aqueous NaBH4 treatment. Reaction of compound (19) with bromine in methanol afforded 11 -bromo-10-methoxy-3, 9-propano-8-aza-9H-xanthine (28). The latter on stereochemically controlled elimination with DBU led to 10-methoxy-3, 9-propeno- 8-aza-9H-xanthine (29), easily converted into 11-bromo-10, 12-dimethoxy-3, 9- propano-8-aza-9H-xanthine(30).
Izvorni jezik
Engleski
Znanstvena područja
Kemija
POVEZANOST RADA
Ustanove:
Institut "Ruđer Bošković", Zagreb
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- SCI-EXP, SSCI i/ili A&HCI
