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A convenient synthesis of tricyclic purine derivatives
Author(s) -
Shimada Junichi,
Kuroda Takeshi,
Suzuki Fumio
Publication year - 1993
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.5570300141
Subject(s) - chemistry , tricyclic , thionyl chloride , purine , methylation , stereochemistry , chloride , medicinal chemistry , organic chemistry , combinatorial chemistry , dna , biochemistry , enzyme
A convenient synthesis of new heterocycles such as 7,8‐dihydro‐1 H ‐imidazo[2,1‐ i ]purin‐5(4 H )‐ones ( 2 , n = 0) and 5,6‐dihydro‐1 H ‐imidazo[2,1‐ b ]purin‐9(8 H )‐ones ( 3 ) was described. The syntheses of 2 and 3 were accomplished by treatment of 6‐methylthio‐7 H ‐purin‐2(3‐ H )‐ones 7 or 2‐benzylthio‐1‐methyl‐9‐triphenylmethyl‐9 H ‐purin‐6(1 H )‐one ( 15 ) with appropriate aminoalcohol followed by dehydrative cyclization using thionyl chloride. Compound 15 was efficiently prepared by benzylation of 6‐hydroxy‐2‐mercaptopurine ( 12 ) followed by tritylation and N ‐methylation.