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The synthesis and PMR study of certain 3‐substituted 2‐(β‐D‐Ribofuranosyl)indazoles
Author(s) -
Revankar Ganapathi R.,
Townsend Leroy B.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070615
Subject(s) - chemistry , indazole , anomer , bromide , trimethylsilyl , stereochemistry , anomeric effect , medicinal chemistry , organic chemistry
Abstract The synthesis of 3‐cyano‐2‐(β‐D‐ribofuranosyl)indazole (4) has been accomplished by a condensation of N ‐trimethylsilyl‐3‐cyanoindazole (1) with 2,3,5‐tri‐ O ‐aeetyl‐D‐ribofuranosyl bromide (2) followed by subsequent deacetylation. The reactivity of the 3‐cyano group was demonstrated by the conversion of 4 to 2‐(β‐D‐ribofuranosyl)indazole‐3‐carboxamide (5) and 2‐(β‐D‐ribofuranosyl)indazole‐3‐thiocarboxamide (6). The site of ribosylation and the assignment of anomeric configuration for 4 is discussed. The magnetic anisotropy effect of the exocyclic group at C3 on the anomeric proton as determined by pmr spectroscopy is discussed.