A convenient synthesis of tricyclic purine derivatives | Zendy

Shimada Junichi | Zendy; Kuroda Takeshi | Zendy; Suzuki Fumio | Zendy

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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.

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