791856-65-0Relevant academic research and scientific papers
Synthesis of meta-Functionalized Pyridines by Selective Dehydrogenative Heterocondensation of β- and γ-Amino Alcohols
Hille, Toni,Irrgang, Torsten,Kempe, Rhett
supporting information, p. 371 - 374 (2016/12/30)
New reactions that convert alcohols into important classes of compounds are becoming increasingly important as their development contributes to the conservation of our fossil carbon feedstock and the reduction of CO2emissions. Two key catalytic alcohol conversion concepts are borrowing hydrogen or hydrogen autotransfer and acceptorless dehydrogenative condensation. Herein, we combined both concepts to synthesize meta-functionalized pyridines. First, diols and amines were linked to β-amino alcohols, which can then undergo a selective dehydrogenative heterocondensation with γ-amino alcohols. Iridium catalysts stabilized by PN5P pincer ligands that were developed in our laboratory mediate the reactions most efficiently. All of the 3-aminopyridines that we describe in this paper have been synthesized for the first time, emphasizing the degree of innovation of this method and the problems associated with the synthesis of such meta-functionalized pyridines.
Ruthenium-Catalyzed Straightforward Synthesis of 1,2,3,4-Tetrahydronaphthyridines via Selective Transfer Hydrogenation of Pyridyl Ring with Alcohols
Xiong, Biao,Li, Ya,Lv, Wan,Tan, Zhenda,Jiang, Huanfeng,Zhang, Min
supporting information, p. 4054 - 4057 (2015/09/01)
Through a ruthenium-catalyzed selective hydrogen transfer coupling reaction, a novel straightforward synthesis of 1,2,3,4-tetrahydronaphthyridines from o-aminopyridyl methanols and alcohols has been developed. The synthetic protocol proceeds in an atom- a
Intramolecular inverse-electron-demand Diels-Alder reactions of imidazoles with 1,2,4-triazines: A new route to 1,2,3,4-tetrahydro-1,5-naphthyridines and related heterocycles
Lahue, Brian R.,Lo, Sie-Mun,Wan, Zhao-Kui,Woo, Grace H. C.,Snyder, John K.
, p. 7171 - 7182 (2007/10/03)
The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.
