100
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Regioselective Synthesis of Indazole N1‐ and N2‐(βd‐Ribonucleosides)

&
Pages 227-237 | Received 22 Aug 2003, Accepted 06 Oct 2003, Published online: 01 Jun 2007
 

Abstract

The regioselective synthesis of 4‐nitroindazole N 1‐ and N 2‐(βd‐ribonucleosides) (8, 9, 1b and 2b) is described. The N 1‐regioisomers are formed under thermodynamic control of the glycosylation reaction [fusion reaction or Silyl Hilbert‐Johnson glycosylation for 48 h (66%)], while the kinetic control (Silyl Hilbert‐Johnson glycosylation for 5 h) afforded only the N 2‐isomer (64%). The structures of the nucleosides 1b and 2b were assigned by single crystal X‐ray analyses. The 4‐amino‐N 1‐(βd‐ribofuranosyl)‐1H‐indazole (3b) was obtained from the nitro nucleoside 1b by catalytic hydrogenation. Compound 3b shows fluorescence while the 4‐nitroindazole nucleosides 1b and 2b do not possess this property.

In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

Acknowledgments

The authors thank Dr. H. Rosemeyer and Dr. Y. He for the measurement of the 1H‐ and 13C‐NMR spectra. We gratefully acknowledge financial support by the European Community (grant no.: QLRT‐2001‐00506, “Flavitherapeutics”).

Notes

In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 606.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.