The synthesis of 2‐azainosine and related derivatives by ring annulation of imidazole nucleosides | Zendy

Panzica Raymond P. | Zendy; Townsend Leroy B. | Zendy

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The synthesis of 2‐azainosine and related derivatives by ring annulation of imidazole nucleosides

Author(s) -

Panzica Raymond P.,

Townsend Leroy B.

Publication year - 1972

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.5570090324

Subject(s) - chemistry , annulation , riboside , ring (chemistry) , imidazole , stereochemistry , bicyclic molecule , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry

The synthesis of 7‐(β‐D‐ribofuranosyl)imidazo[4,5‐ d ]‐ v ‐triazin‐4‐one ( 6b , 2‐azainosine) and 5‐(β‐D‐ribofuranosyl)imidazo[4,5‐ d ]‐ v ‐triazin‐4‐one ( 4b ) have been achieved for the first time by direct diazotization of AICA riboside ( 5b ) and iso ‐AICA riboside ( 3b ), respectively. The conditions required for cyclization of the model methyl bases, 3a and 5a , as well as the nucleosides 3b , 5b , and 7 are described.

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