Straightforward Pyrimidine Ring Construction: A Versatile Tool for the Synthesis of Nucleobase and Nucleoside Analogues | Zendy

Robin Aélig | Zendy; Julienne Karine | Zendy; Meslin JeanClaude | Zendy; Deniaud David | Zendy

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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)

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