152563-03-6Relevant articles and documents
Copper- and Cobalt-Catalyzed Syntheses of Thiophene-Based Tertiary Amines
Bouarfa, Salima,Gra?l, Simon,Ivanova, Maria,Langlais, Timothy,Bentabed-Ababsa, Ghenia,Lassagne, Frédéric,Erb, William,Roisnel, Thierry,Dorcet, Vincent,Knochel, Paul,Mongin, Florence
, p. 3244 - 3258 (2019/06/08)
Thienylzinc halides and related compounds prepared by deprotonation followed by transmetalation were used in copper-catalyzed amination using N-benzoyloxy secondary amines. By extending the reaction to 1,5-naphthyridine, it was showed that the competitive dimer formation observed in the case of thiophenes was linked with the low stability of some thienylamines rather than homocoupling. Interestingly, thienylzinc halides and related compounds prepared by transmetalation of thienylmagnesium halides, either prepared from their bromo-precursors or generated by deprotometalation, were satisfactorily employed in cobalt-catalyzed aminations. Finally, aminothiophenes were involved in copper-catalyzed mono- and di-N-arylations, affording differently substituted di- and triphenylamines.
Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl)
Balkenhohl, Moritz,Greiner, Robert,Makarov, Ilya S.,Heinz, Benjamin,Karaghiosoff, Konstantin,Zipse, Hendrik,Knochel, Paul
, p. 13046 - 13050 (2017/09/06)
A set of successive regioselective metalations and functionalizations of the 1,5-naphthyridine scaffold are described. A combination of Zn-, Mg-, and Li-TMP (TMP=2,2,6,6-tetramethylpiperidyl) bases and the presence or absence of a Lewis acid (BF3?OEt2) allows the introduction of up to three substituents to the 1,5-naphthyridine core. Also, a novel “halogen dance” reaction was discovered upon metalation of an 8-iodo-2,4-trifunctionalized 1,5-naphthyridine allowing a fourth regioselective functionalization. Additionally, reactions leading to key 1,5-naphthyridines for the preparation of OLED materials and a potential antibacterial agent were performed.
Amination and Synthesis of Some Nitronaphthyridines
Wozniak, Marian,Tomula, Maria
, p. 471 - 476 (2007/10/02)
3-Nitro and 3,6-dinitro-1,8-naphthyridines 1, 4 and 5 are dehydroaminated with a liquid ammonia solution of potassium permanganate to the corresponding 4-amino-substituted compounds 3, 8 and 9.The intermediate 4-amino ?-adducts 2,6 and 7 of the nitro-1,8-naphthyridines are detected by 1H-NMR spectroscopy.The syntheses of some nitro-substituted naphthyridines are described. Key Words: Amination / Amino ?-adducts / Naphthyridines