36022-11-4Relevant articles and documents
Cross-Coupling Reactions of Monosubstituted Tetrazines
Hoff, Lukas V.,Schnell, Simon D.,Tomio, Andrea,Linden, Anthony,Gademann, Karl
supporting information, p. 5689 - 5692 (2021/08/16)
A Ag-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids is presented. Electronic modification of the 1,1′-bis(diphenylphosphine)ferrocene (dppf) ligand was found to be crucial for good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were prepared (29 examples, up to 87% yield).
Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines
Schnell, Simon D.,González, Jorge A.,Sklyaruk, Jan,Linden, Anthony,Gademann, Karl
, p. 12008 - 12023 (2021/08/24)
Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.
Synthesis of 3-Phenyl-5-silylpyridazines by Regioselective -Cycloadditions
Birkofer, Leonhard,Haensel, Edward,Steigel, Alois
, p. 2574 - 2585 (2007/10/02)
The cycloaddition of 3-phenyl-1,2,4,5-tetrazine (1) with the silylethyne 2a proceeds highly regioselectively to give 3-phenyl-5-(trimethylsilyl)pyridazine (3a).Similarly the reactions of 1 with the silylalkynes 2b - f, the silylalkynones 2g - i, and the s