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Straightforward Pyrimidine Ring Construction: A Versatile Tool for the Synthesis of Nucleobase and Nucleoside Analogues
Author(s) -
Robin Aélig,
Julienne Karine,
Meslin JeanClaude,
Deniaud David
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.200500556
Subject(s) - chemistry , pyrimidine , nucleobase , nucleoside , ring (chemistry) , combinatorial chemistry , stereochemistry , iodide , organic chemistry , dna , biochemistry
A general route to 1,2,4‐trisubstituted pyrimidines is described in one to three steps from a common key precursor, diazadienium iodide 2 . An efficient preliminary [4+2] cyclocondensation reaction between the azabutadiene building block 2 and various iso(thio)cyanates constitutes an original construction of the pyrimidine skeleton. Subsequent structural modifications on the heterocycle allow the elaboration of a 1‐substituted pyrimidine library that includes nucleoside analogues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)