54629-30-0Relevant articles and documents
Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation
Marquise, Nada,Harford, Philip J.,Chevallier, Floris,Roisnel, Thierry,Dorcet, Vincent,Gagez, Anne-Laure,Sablé, Sophie,Picot, Laurent,Thiéry, Valérie,Wheatley, Andrew E.H.,Gros, Philippe C.,Mongin, Florence
, p. 10123 - 10133 (2013/11/06)
The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6- tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents.
Intramolecular Anionic Friedel-Crafts Equivalents. A General Regiospecific Route to Substituted and Naturally Occurring Xanthen-9-ones
Familoni,Ionica, Ileana,Bower, Justin F.,Snieckus, Victor
, p. 1081 - 1083 (2007/10/03)
An LDA-induced regiospecific and general conversion of diaryl ether 2-carboxamides 4 into substituted xanthones 5, including natural products, 2-hydroxy-1-methoxyxanthone (8) and 6-deoxyjacareubin (14), is described.
Directed Lithiation of 4-Halopyridines: Chemoselectivity, Regioselectivity and Application to Synthesis
Marsais, F.,Trecourt, F.,Breant, P.,Queguiner, G.
, p. 81 - 87 (2007/10/02)
4-Chloro and 4-fluoropyridines were ortho-lithiated by n-butyllithium-TMEDA chelate or lithium diisopropylamide at low temperature.The resulting 3-lithio 4-halopyridines were reacted with electrophiles which led to various 3,4-disubstituted pyridines.The versatility of this functionalization is enhanced by the 4-halogen reactivity towards nucleophiles such as water, methylate and amines.Some of the 3,4-disubstituted synthons were annelated to naphthyridine, xanthone and coumarin or condensed to Hantzsch-ester or to "chlotrimazol" analogues.Lithiation of 4-fluoropyridine led in one step to 3,4-pyridyne, which was trapped by cycloaddition with furans.