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Synthesis of Purines Bearing Functionalized C‐Substituents by the Conjugate Addition of Nucleophiles to 6‐Vinylpurines and 6‐Ethynylpurines
Author(s) -
Kuchař Martin,
Pohl Radek,
Votruba Ivan,
Hocek Michal
Publication year - 2006
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.200600545
Subject(s) - chemistry , purine metabolism , conjugate , nucleophile , purine , electrophile , organic chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , catalysis , enzyme , mathematical analysis , mathematics
Abstract Purines bearing diverse β‐substituted ethyl or vinyl groups in position 6 were prepared by the conjugate addition of N‐, O‐ and S‐nucleophiles to 6‐vinylpurines or 6‐ethynylpurines. The scope of this methodology was systematically studied. The addition of amines, alcoholates and thiolates to 6‐vinylpurines gave the corresponsing 6‐(2‐aminoethyl)‐, 6‐(2‐alkoxyethyl)‐ and 6‐[2‐(alkylsulfanyl)ethyl]purines. The addition of amines to 6‐ethynylpurines gave 6‐(2‐aminovinyl)purines, while the addition of alcoholates and thiolates gave 6‐(2‐dialkoxyethyl)‐ and 6‐[2‐bis(alkylsulfanyl)ethyl]purines. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)