The synthesis of 3‐(β‐D‐ribofuranosyl)imidazo[4,5‐ c ] pyridazines | Zendy

Halverson D. Michael | Zendy; Castle Raymond N. | Zendy

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The synthesis of 3‐(β‐D‐ribofuranosyl)imidazo[4,5‐ c ] pyridazines

Author(s) -

Halverson D. Michael,

Castle Raymond N.

Publication year - 1974

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.5570110108

Subject(s) - pyridazine , chemistry , bromide , condensation , anomer , medicinal chemistry , stereochemistry , organic chemistry , physics , thermodynamics

7‐Chloro‐3‐(β‐ D ‐2,3,5‐tri‐ O ‐benzoylribofuranosyl)imidazo[4,5‐ c ] pyridazine ( 3 ), obtained from the condensation of 7‐chloro‐3‐trimethylsilylimidazo[4,5‐ c ] pyridazine ( 1 ) with 2,3,5‐tri‐ O ‐benzoyl‐ D ‐ribofuranosyl bromide ( 2 ), served as the percursor of 7‐chloro‐ ( 4 ), 7‐amino‐ ( 8 ), and 7‐mercapto‐3‐(β‐ D ‐ribofuranosyl)imidazo[4,5‐ c ] pyridazine ( 9 ). 3‐(β‐ D ‐ribofuranosyl)imidazo[4,5‐ c ] pyridazine ( 7 ) was obtained from 3‐(β‐ D ‐2,3,5‐tri‐ O ‐benzoylribofuranosyl)imidazo‐[4,5‐ c ]pyridazine ( 6 ). The site of ribosidation is based upon uv spectral comparisons with model methyl compounds. The assignment of the anomeric configuration is derived from pmr spectral data.

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