Regioselective Preparation of N7- and N9-Alkyl Derivatives of N6-[(Dimethylamino)methylene]adenine Bearing an Active Methylene Group and Their Further Derivatization Leading to α-Branched Acyclic Nucleoside Analogues
✍ Scribed by Dana Hocková; Miloš Buděšínský; Radek Marek; Jaromír Marek; Antonín Holý
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 341 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Milos ˇBude ˇs ˇı ´nsky ´,[a] Radek Marek, [b] Jaromı ´r Marek, [b] and Antonı ´n Holy ´[a] Keywords: Nucleosides / Acyclic analogues / Purines / Alkylations / 15 N NMR N 7 -and N 9 -regioisomers of cyanomethyl and trifluoroethyl-order to modify their side chain. In this way, several new αbranched acyclic adenosine analogues (8, 10-16) were N 6 -[(dimethylamino)methylene]adenine (1, 2, 6, 7) were prepared regioselectively, the former by the direct alkylation prepared; the regioselectivity of the alkylation and the product structures were determined by 1 H-and 13 C-NMR of N 6 -[(dimethylamino)methylene]adenine, the latter by the alkylation of adenine followed by protection of the amino spectroscopy. 15 N-NMR parameters for selected compounds were studied by gradient-enhanced inverse-detected group. These derivatives, which bear an active methylene group, were submitted to reactions with allyl bromide, techniques. In addition, X-ray data of derivatives 1, 2 and 7 are reported. aldehydes or tert-butoxybis(dimethylamino)methane in usually either the Mitsunobu reaction [8] or building up of a [a] Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, mixture of 7-and 9-alkyl derivatives of N 6 -[(dimethyl-Flemingovo na ´m. 2, CZ-16610 Prague 6, Czech Republic amino)methylene]adenine was reported), [11] only 7-alkyl E-mail: (D. H.