Functionalization of Guanosine and 2′‐Deoxyguanosine at C6: A Modified Appel Process and S_NAr Displacement of Imidazole

References

• Zhong , M. and Robins , M. J. in press . Regioisomers in Vorbrüggen's guanine nucleoside synthesis; N9 selectivity with a glucosamine derivative and 2‐N‐acetyl‐6‐O‐diphenylcarbamoylguanine . Tetrahedron Lett. , [CSA]
   Web of Science ®Google Scholar
• Miles , R. W. , Samano , V. and Robins , M. J. 1995 . Nucleic acid related compounds. 86. Nucleophilic functionalization of adenine, adenosine, tubercidin, and formycin derivatives via elaboration of the heterocyclic amino group into a readily displaced 1,2,4‐triazol‐4‐yl substituent . J. Am. Chem. Soc. , 117 : 5951 – 5957 .
   Web of Science ®Google Scholar
• Gerster , J. F. , Jones , J. W. and Robins , R. K. 1963 . Purine nucleosides. IV. The synthesis of 6‐halogenated 9‐β‐d‐ribofuranosylpurines from inosine and guanosine . J. Org. Chem. , 28 : 945 – 948 .
   Web of Science ®Google Scholar
• Robins , M. J. and Uznanski , B. 1981 . Nucleic acid related compounds. 33. Conversions of adenosine and guanosine to 2,6‐dichloro, 2‐amino‐6‐chloro, and derived purine nucleosides . Can. J. Chem. , 59 : 2601 – 2607 .
   Web of Science ®Google Scholar
• Janeba , Z. , Francom , P. and Robins , M. J. 2003 . Efficient syntheses of 2‐chloro‐2′‐deoxyadenosine (cladribine) from 2′‐deoxyguanosine . J. Org. Chem. , 68 : 989 – 992 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Véliz , E. A. and Beal , P. 2001 . 6‐Bromopurine nucleosides as reagents for nucleoside analogue synthesis . J. Org. Chem. , 66 : 8592 – 8598 . [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Robins , M. J. and Uznanski , B. 1981 . Nucleic acid related compounds. 34. Nonaqueous diazotization with tert‐butyl nitrite. Introduction of fluorine, chlorine, and bromine at C‐2 of purine nucleosides . Can. J. Chem. , 59 : 2608 – 2611 .
   Web of Science ®Google Scholar
• Nair , V. and Richardson , S. G. 1982 . Modification of nucleic acid bases via radical intermediates: synthesis of dihalogenated purine nucleosides . Synthesis , : 670 – 672 . [CROSSREF]
   Web of Science ®Google Scholar
• Volpini , R. , Costanzi , S. , Lambertucci , C. , Taffi , S. , Vittori , S. , Klotz , K.‐N. and Cristalli , G. 2002 . N 6‐alkyl‐2‐alkynyl derivatives of adenosine as potent and selective agonists at the human adenosine A3 receptor and a starting point for searching A2B ligands . J. Med. Chem. , 45 : 3271 – 3279 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Francom , P. , Janeba , Z. , Shibuya , S. and Robins , M. J. 2002 . Nucleic acid related compounds. 116. Nonaqueous diazotization of aminopurine nucleosides. Mechanistic considerations and efficient procedures with tert‐butyl nitrite or sodium nitrite . J. Org. Chem. , 67 : 6788 – 6796 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Francom , P. and Robins , M. J. 2003 . Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6‐halo‐and 2,6‐dihalopurine nucleosides and 2′‐deoxynucleosides with acyl or silyl halides . J. Org. Chem. , 68 : 666 – 669 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Gao , H. , Fathi , R. , Gaffney , B. L. , Goswami , B. , Kung , P.‐P. , Rhee , Y. , Jin , R. and Jones , R. A. 1992 . 6‐O‐(pentafluorophenyl)‐2′‐deoxyguanosine: a versatile synthon for nucleoside and oligonucleotide synthesis . J. Org. Chem. , 57 : 6954 – 6959 .
   Web of Science ®Google Scholar
• Fathi , R. , Goswami , B. , Kung , P.‐P. , Gaffney , B. L. and Jones , R. A. 1990 . Synthesis of 6‐substituted 2′‐deoxyguanosine derivatives using trifluoroacetic anhydride in pyridine . Tetrahedron Lett. , 31 : 319 – 322 . [CROSSREF]
   Web of Science ®Google Scholar
• Gaffney , B. L. and Jones , R. A. 1982 . Synthesis of O‐6‐alkylated deoxyguanosine nucleosides . Tetrahedron Lett. , 23 : 2253 – 2256 . [CROSSREF]
   Web of Science ®Google Scholar
• Lakshman , M. K. , Ngassa , F. N. , Keeler , J. C. , Dinh , Y. Q.V. , Hilmer , J. H. and Russon , L. M. 2000 . Facile synthesis of O 6‐alkyl‐, O 6‐aryl‐, and diaminopurine nucleosides from 2′‐deoxyguanosine . Org. Lett. , 2 : 927 – 930 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Lakshman , M. K. and Gunda , P. 2003 . Palladium‐catalyzed synthesis of carcinogenic polycyclic aromatic hydrocarbon epoxide‐nucleoside adducts: the first amination of a chloro nucleoside . Org. Lett. , 5 : 39 – 42 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Lakshman , M. K. , Hilmer , J. H. , Martin , J. Q. , Keeler , J. C. , Dinh , Y. Q.V. , Ngassa , F. N. and Russon , L. M. 2001 . Palladium catalysis for the synthesis of hydrophobic C‐6 and C‐2 aryl 2′‐deoxynucleosides. Comparison of C–C versus C–N bond formation as well as C‐6 versus C‐2 reactivity . J. Am. Chem. Soc. , 123 : 7779 – 7787 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• De Riccardis , F. and Johnson , F. 2000 . Chemical synthesis of cross‐linked purine nucleosides . Org. Lett. , 2 : 293 – 295 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Lakshman , M. K. , Keeler , J. C. , Hilmer , J. H. and Martin , J. Q. 1999 . Palladium‐catalyzed C–N bond formation: facile and general synthesis of N 6‐aryl 2′‐deoxyadenosine analogues . J. Am. Chem. Soc. , 121 : 6090 – 6091 . [CROSSREF]
   Web of Science ®Google Scholar
• Appel , R. 1975 . Tertiary phosphane/tetrachloromethane, a versatile reagent for chlorination, dehydration, and P–N linkage . Angew. Chem., Int. Ed. Engl. , 14 : 801 – 811 . [CROSSREF]
   Web of Science ®Google Scholar
• Castro , B. R. 1983 . Replacement of alcoholic hydroxyl groups by halogens and other nucleophiles via oxyphosphonium intermediates . Org. React. , 29 : 1 – 162 .
   Web of Science ®Google Scholar
• Lin , X. and Robins , M. J. 2000 . Mild and efficient functionalization at C6 of purine 2′‐deoxynucleosides and ribonucleosides . Org. Lett. , 2 : 3497 – 3499 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Lin , X. 2002 . Ph.D. Dissertation Brigham Young University .
   Google Scholar
• Matsuda , A. , Shinozaki , M. , Suzuki , M. , Watanabe , K. and Miyasaka , T. 1986 . A convenient method for the selective acylation of guanine nucleosides . Synthesis , : 385 – 386 . [CROSSREF]
   Web of Science ®Google Scholar
• Schaller , H. , Weimann , G. , Lerch , B. and Khorana , H. G. 1963 . Studies on polynucleotides. XXIV. The stepwise synthesis of specific deoxyribopolynucleotides (4). Protected derivatives of deoxyribonucleosides and new syntheses of deoxyribonucleoside‐3′ phosphates . J. Am. Chem. Soc. , 85 : 3821 – 3927 .
   Web of Science ®Google Scholar
• Daskalov , H. P. , Sekine , M. and Hata , T. 1981 . Synthesis and properties of O 6‐substituted guanosine derivatives . Bull. Chem. Soc. Jpn. , 54 : 3076 – 3083 .
   Web of Science ®Google Scholar
• Naito , T. , Ueno , K. and Ishikawa , F. 1964 . Studies on nucleosides and nucleotides. VII. Synthesis of 2‐amino‐6‐substituted‐9‐β‐d‐ribofuranosylpurines . Chem. Pharm. Bull. , 12 : 951 – 954 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Bressi , J. C. , Choe , J. , Hough , M. T. , Buckner , F. S. , Van Voorhis , W. C. , Verlinde , C. L.M.J. , Hol , W. G.J. and Gelb , M. H. 2000 . Adenosine analogues as inhibitors of Trypanosoma brucei phosphoglycerate kinase: elucidation of a novel binding mode for a 2‐amino‐N6‐substituted adenosine . J. Med. Chem. , 43 : 4135 – 4150 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Milne , G. H. and Townsend , L. B. 1974 . Synthesis and antitumor activity of α‐and β‐2′‐deoxy‐6‐selenoguanosine and certain related derivatives . J. Med. Chem. , 17 : 263 – 268 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Segal , A. , Solomon , J. J. , Maté , U. and Van Duuren , B. L. 1982 . Formation of 6‐dimethylcarbamyloxy‐dGuo, 6‐dimethylamino‐dGuo and 4‐dimethylamino‐dThd following in vitro reaction of dimethylcarbamyl chloride with calf thymus DNA and 6‐diethycarbamyloxy‐dGuo following in vitro reaction of diethylcarbamyl chloride with calf thymus DNA . Chem. Biol. Interact. , 40 : 209 – 231 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar