Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction
| Autor: | Radim Nencka, Martin Dračínský, Michal Šála, Juraj Galeta, Zdeněk Havlas, Milan Vrabel |
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| Rok vydání: | 2016 |
| Předmět: |
Pyrimidine
010405 organic chemistry Organic Chemistry Regioselectivity Single step 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Tetrazine chemistry.chemical_compound Deprotonation chemistry Cascade reaction Structural isomer Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 18:3594-3597 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.6b01601 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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