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Synthesis of 6‐(pyrrol‐1‐yl)purine and of some of its 9‐glycosides
Author(s) -
Haidoune M'Barek,
Mornet René
Publication year - 1994
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.5570310629
Subject(s) - chemistry , purine , glycosyl , glycoside , hydrolysis , acetic acid , purine metabolism , methanol , organic chemistry , acid hydrolysis , stereochemistry , enzyme
Adenine reacts slowly with 2,5‐dimethoxytetrahydrofuran ( 3 ) in a dilute acetic acid solution in methanol‐water, to give 6‐(pyrrol‐1‐yl)purine ( 4 ). Under more acidic conditions, 4 is partly transformed to 6‐(indol‐1‐yl)purine ( 5 ) and other unidentified products. The reaction may be used for the preparation of 9‐glycosides of 4 from the corresponding adenine derivatives provided their 9‐glycosyl linkage is somewhat resistant to acid hydrolysis.