REFERENCES
- Fox , J. J. , Watanabe , K. A. and Bloch , A. 1966 . Progress in Nucleic Acid Research and Molecular Biology , Edited by: Davidson , J. N. and Cohn , W. E. p. 251 Academic Press .
- Venulet , J. and VanEtten , L. 1970 . The chemistry of the nitro and nitroso group Part 2 , Edited by: Feuer , H. p. 201 Interscience Publishers .
- Ohta , N. , Minamoto , K. , Yamamoto , T. , Koide , N. and Sakoda , S. 1996 . Nucleosides Nudeotides , 15 : 833 – 855 .
- In this context, the first synthesis of 3′-deoxy-3′-nitrothymidine and its 2′,3′-didehydro analogue as potential anti-AIDS substances has been recorded recently by Hossain et al.5
- Hossain , N , Papchikhin , A. , Garg , N. , Fedorov , L and Chattopadhyaya , J. Nucleosides Nudeotides , 12 499 – 528 .
- Hossain , N. , Garg , N. and Chattopadhyaya , J. 1993 . Tetrahedron , 49 : 10061 – 10068 .
- Beranek , J. , Friedman , H. , Watanabe , K. A. and Fox , J. J. 1965 . J. Heterocycl. Chem. , 2 : 188 – 191 .
- An attempt to isolate compound 6 as a hydrochloride salt has also failed.
- Biffin , M. E. C. , Miller , J. and Paul , D. B. 1971 . The chemistry of azido groupn , Edited by: Patai , S. p. 57 Interscience Publishers .
- Yamamoto , T. , Tsuboike , K. and Minamoto , K. 1996 . Nucleic Acids Symp. Series , 35 : 35 – 36 .
- Similar azide reactions in THF or acetone revealed the formations of compound 11 and a similar amount of a far less polar product (silica gel TLC; CHCl3/EtOH, 9:1). The latter compound was isolated by column chromatography, recrystallized from MeOH at room temperature (mp 178–180°C) and shown to absorb at 2140 cm−1 (N3). However, repeated elemental analyses gave no satisfactory analysis values for this compound probably owing to thermal change to 11. In fact, its partial conversion into 11 was observed by TLC after being heated in MeOH for 30 min. Probably, the more electronegative adenine base would make H-3 more labile, thus rendering the azide insertion of the initially formed Michael adduct more facile. Polarity or basisity of the reaction medium may also influence the insertion. Elimination of nitrous acid from iv would occur rapidly to effect resonance stabilization.
- Huryn , D. M. and Okabe , M. 1992 . Chem. Rev. , 92 : 1745 – 1768 .