Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 3
55
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

AMINO-THIOCYANATION OF ELECTRON RICH OLEFINS AS AN EFFICIENT PURINE AND PYRIMIDINE N-ALKYLATION PROCESS

, , , &
Pages 343-353 | Received 19 Mar 2001, Published online: 16 Aug 2006

REFERENCES

  • Mitsuya , H. , Yarchoan , R. and Broder , S. 1990 . Science , 249 : 1533 – 1543 .
  • Cook , P. 1991 . Dan. Anti-Cancer Drug Design , 6 : 585 – 607 .
  • Abu , S. , Tramontano , E. , Loi , G. , Franchetti , P. , Grifantini , M. and La Colla , P. 1999 . Nucleosides & Nucleotides , 18 ( 4&5 ) : 849 – 851 .
  • Smeijsters , L. , Franssen , F. , Naesens , L. , De Vries , E. , Holy , A. , Balzarini , J. , De Clerq , E. and Overdulve , J. 1999 . Int. J. Antimicrob. Agents , 12 ( 1 ) : 53 – 61 .
  • Meier , C. , Habel , L. , Haller-Meier , F. , Lomp , A. , Herderich , M. , Klocking , R. , Meerbach , A. and Wutzler , P. 1998 . Antiviral Chem. Chemother. , 9 ( 5 ) : 389 – 402 .
  • Wilson , L. , Hager , M. , El-Kattan , A. and Liotta , D. 1995 . Synthesis , : 1465 – 1479 .
  • Diaz , Y. , El-Laghdach , A. and Castillon , S. 1997 . Tetrahedron , 53 ( 31 ) : 10921 – 10938 .
  • Kawakami , H. , Ebata , T. , Koseski , K. , Okano , K. , Katsuya , M. and Matsushita , H. 1993 . Heterocycles , 36 ( 4 ) : 665 – 669 .
  • El-Laghdach , A. , Matheu , M. and Castillon , S. 1994 . Tetrahedron , 50 ( 42 ) : 12219 – 12234 .
  • Wang , J. , Wurster , J. , Wilson , L. and Liotta , D. 1993 . Tet. Lett. , 34 ( 31 ) : 4881 – 4884 .
  • Stewart , D. , Trauth , J. , Windholtz , J. and Church , K. 1996 . Synth. Commun. , 26 ( 22 ) : 4279 – 4288 .
  • El-Laghdach , A. , Diaz , Y. and Castillon , S. 1993 . Tet. Lett. , 34 ( 17 ) : 2821 – 2822 .
  • Vasileva , M. , Bychkova , T. , Ivanova , N. , Dobrynina , L. and Kalabina , A. 1986 . Zh. Org. Khim. , 22 ( 6 ) : 1165 – 1168 .
  • Guy , R. and Pearson , I. 1973 . J. Chem. Soc. Perkin. Trans. I , : 281 – 284 .
  • Niedballa , U. and Vorbruggen , H. 1974 . J. Org. Chem. , 39 ( 25 ) : 3654 – 3660 .
  • Vorbruggen , H. , Krolikiewicz , K. and Bennua , B. 1981 . Chem. Ber. , 114 : 1234 – 1255 .
  • Fuertes , M. , Garcia-Munoz , G. , Madronero , R. and Stud , M. 1972 . Tetrahedron , 28 : 623 – 635 . Proton coupling constants of the protons on C2 and C3 of compounds 1a, 2a, 6 and 7 were used to assign their relative stereochemistry. 1a (J2,3 = 9.9 Hz), 2a (J2,3 = 5.6 Hz), 6 (J2,3 = 10.1), 7 (J2,3 = 5.2 Hz). For examples of coupling constants in these types of systems
  • Leutzinger , E. , Bowles , W. , Robins , R. and Townsend , L. 1968 . J. Amer. Chem. Soc. , 90 ( 1 ) : 150
  • Augustyns , K. , Rozenski , J. , Van Aerschot , A. , Janssen , G. and Herdewijn , P. 1993 . J. Org. Chem. , 58 : 2977 – 2982 .
  • Baud , M. , Chavis , C. , Lucas , M. and Imbach , J. 1991 . Tetrahedron , 47 ( 48 ) : 9993 – 10002 .
  • Bessodes , M. , Lakaf , R. and Antonakis , K. 1986 . Carbohydrate Res. , 148 : 148 – 152 .
  • UV and 13C-NMR (carbon bearing the heterocycle) chemical shift data of the major and minor isomers; 1a and 1b through 5a and 5b Compounds UV (EtOH, nm) 13C NMR (ppm, DMSOd6 ) 1a 234, 281 85.9 1b 234, 281 84.3 2a 233, 281 91.4 2b 233, 281 86.6 3a 231, 282, 329 66.8 3b 231, 282, 329 66.1 4a 233, 280 84.3 4b 232, 279 81.7 5a 231, 280 73.6 5b 231, 280 62.1

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.