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

0463529 - ÚOCHB 2017 RIV US eng J - Článek v odborném periodiku
Galeta, Juraj - Šála, Michal - Dračínský, Martin - Vrábel, Milan - Havlas, Zdeněk - Nencka, Radim
Single-Step Formation of Pyrimido[4,5-d]pyridazines by a Pyrimidine-Tetrazine Tandem Reaction.
Organic Letters. Roč. 18, č. 15 (2016), s. 3594-3597. ISSN 1523-7060. E-ISSN 1523-7052
Grant CEP: GA ČR GA15-09310S; GA ČR GA15-11223S; GA ČR GJ15-06020Y; GA ČR(CZ) GBP208/12/G016
Institucionální podpora: RVO:61388963
Klíčová slova: heterocycles * organic synthesis * DFT calculations
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 6.579, rok: 2016

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.
Trvalý link: http://hdl.handle.net/11104/0262703