Single-Step Formation of Pyrimido[4,5‑d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction

A straightforward synthesis of pyrimido­[4,5-d]­pyridazines from pyrimidines and tetrazines under basic conditions is reported. Deprotonated, substituted 5-halopyrimidines readily react with variously substituted tetrazines in a highly regioselective manner via a complex reaction pathway, which was...

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Bibliographic Details
Published in:Organic letters 2016-08, Vol.18 (15), p.3594-3597
Main Authors: Galeta, Juraj, Šála, Michal, Dračínský, Martin, Vrábel, Milan, Havlas, Zdeněk, Nencka, Radim
Format: Article
Language:English
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Summary:A straightforward synthesis of pyrimido­[4,5-d]­pyridazines from pyrimidines and tetrazines under basic conditions is reported. Deprotonated, substituted 5-halopyrimidines readily react with variously substituted tetrazines in a highly regioselective manner via a complex reaction pathway, which was supported by DFT calculations. This mechanism leads to the empirically observed regioisomers without going through the conceivable hetaryne intermediate. These results on 5-halopyrimidines led to development of the methodology for preparation of opposite regioisomers based on 6-halopyrimidines.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01601