- An efficient synthesis of substituted cytosines and purines under focused microwave irradiation
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A rapid nucleophilic displacement reaction of 6-chloropurine, 2-amino-6-chloropurine and 5-bromocytosine with various nucleophiles under focused microwave irradiation is described. Using this method, the desired products were obtained with the yields up to 99% in?a?short reaction time.
- Huang, Ling-Kuen,Cherng, Yen-Chih,Cheng, Yann-Ru,Jang, Jing-Pei,Chao, Yi-Ling,Cherng, Yie-Jia
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p. 5323 - 5327
(2008/02/01)
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- An efficient one-pot synthesis of 6-alkoxy-8,9-dialkylpurines via reaction of 5-amino-4-chloro-6-alkylaminopyrimidines with N,N-dimethylalkaneamides and alkoxide ions
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The synthesis of a number of new 6-alkoxy-8,9-(disubstituted)purines has been accomplished by the cyclization of the corresponding intermediate 5-amino-4-chloro-6-(alkylamino)pyrimidines promoted by alkoxides and various N,N-dimethyl amides, where the latter act as solvent-reagents. By this three-component condensation reaction we are able to introduce an alkyl group in the 8 position of the purine ring with the concomitant nucleophilic replacement of the 6-chloro group with an alkoxy moiety.
- Baraldi, Pier Giovanni,Broceta, Asier Unciti,Infantas, Maria Josè Pineda De Las,Mochun, Juan Josè Dìaz,Espinosa, Antonio,Romagnoli, Romeo
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p. 7607 - 7611
(2007/10/03)
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- N7-DNA: Base-pairing properties of N7-(2'-deoxy-β-d-erythro- pentofuranosyl)-substituted adenine, hypoxanthine, and guanine in duplexes with parallel chain orientation
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Oligonucleotides containing N7-(2'-deoxy-β-D-erythro- pentofuranosyl)adenine (1), -hypoxanthine (2), and -guanine (3) were synthesized on solid-phase using phosphonate and phosphoramidite chemistry. As part of the synthesis of compound 2, the nucleobase-anion glycosylation of various 6-alkoxypurines with 2-deoxy-3,5-di-O-(4-toluoyl)-α-D-erythro- pentofuranosyl chloride (5) was investigated. The duplex stability of oligonucleotides containing N7-glycosylated purines opposite to regular pyrimidines was determined, and thermodynamic data were calculated from melting profiles. Oligodeoxyribonucleotide duplexes containing N7- glycosylated adenine. T(d) or N7-glycosylated guanine C(d) base pairs are more stable in the case of parallel strand orientation than in the case of antiparallel chains.
- Seela, Frank,Leonard, Peter
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p. 2244 - 2263
(2007/10/03)
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