Synthetic Studies Directed towards Agelasine Analogs – Synthesis, Tautomerism, and Alkylation of 2‐Substituted  N ‐Methoxy‐9‐methyl‐9 H ‐purin‐6‐amines | Zendy

Roggen Heidi | Zendy; Gundersen LiseLotte | Zendy

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Synthetic Studies Directed towards Agelasine Analogs – Synthesis, Tautomerism, and Alkylation of 2‐Substituted N ‐Methoxy‐9‐methyl‐9 H ‐purin‐6‐amines

Author(s) -

Roggen Heidi,

Gundersen LiseLotte

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800627

Subject(s) - chemistry , tautomer , alkylation , bromide , medicinal chemistry , alkoxy group , stereochemistry , chlorine atom , alkyl , benzyl bromide , organic chemistry , catalysis

N ‐Methoxy‐9‐methyl‐9 H ‐purin‐6‐amines, carrying various substituents in the 2 positions, were synthesized by the N ‐methylation of known 6‐chloropurines, followed by a displacement of the chlorine. Great variations in the amino/imino tautomer ratio among the compounds studied were observed. The tautomers were identified by NMR methods. Treatment of N ‐methoxy‐9‐methyl‐9 H ‐purin‐6‐amines carrying alkyl, alkoxy, or amino substituents in the 2 position with benzyl bromide resulted in a mixture of N ‐7‐ and N 6 ‐benzylated compounds with the former as the major products. N ‐Methoxy‐9‐methyl‐9 H ‐purin‐6‐amines with strongly electronegative substituents at C‐2 hardly reacted at all under the same set of reaction conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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