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Galeta J, Šála M, Dračínský M, et al. Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction. Org Lett. 2016;18(15):3594-7doi: 10.1021/acs.orglett.6b01601.
Galeta, J., Šála, M., Dračínský, M., Vrábel, M., Havlas, Z., & Nencka, R. (2016). Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction. Organic letters, 18(15), 3594-7. https://doi.org/10.1021/acs.orglett.6b01601
Galeta, Juraj, et al. "Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction." Organic letters vol. 18,15 (2016): 3594-7. doi: https://doi.org/10.1021/acs.orglett.6b01601
Galeta J, Šála M, Dračínský M, Vrábel M, Havlas Z, Nencka R. Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction. Org Lett. 2016 Aug 05;18(15):3594-7. doi: 10.1021/acs.orglett.6b01601. Epub 2016 Jul 08. PMID: 27391276.
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Org Lett. 2016 Aug 05;18(15):3594-7. doi: 10.1021/acs.orglett.6b01601. Epub 2016 Jul 08.

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

Organic letters

Juraj Galeta, Michal Šála, Martin Dračínský, Milan Vrábel, Zdeněk Havlas, Radim Nencka

Affiliations

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Flemingovo nám. 2, 166 10 Prague, Czech Republic.

PMID: 27391276 DOI: 10.1021/acs.orglett.6b01601

Abstract

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.

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