Efficient two-step access to azafluorenones and related compounds

TETRAHEDRON LETTERS

卷:54

Article

Marquise, Nada¹  Harford, Philip J.²  Chevallier, Floris¹  Roisnel, Thierry³  Wheatley, Andrew E. H.²  Gros, Philippe C.⁴  Mongin, Florence¹ 

[1] Univ Rennes 1, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France

[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[3] Univ Rennes 1, CNRS, Inst Sci Chim Rennes, Ctr Diffractometrie X,UMR 6226, F-35042 Rennes, France

[4] Univ Lorraine, CNRS, SRSMC, HECRIN, F-54506 Vandoeuvre Les Nancy, France

关键词: Deprotometallation;    Copper;    Lithium;    Heterocycle;    Palladium;   

DOI  :  10.1016/j.tetlet.2013.04.020

来源: Elsevier

【 摘 要 】

Crystals of a lithiocuprate prepared from copper(I) chloride and lithium 2,2,6,6-tetramethylpiperidide (2 equiv) were isolated and analyzed by X-ray diffraction as (TMP)(2)Cu(Cl)Li-2 center dot THF. The observation of this species is consistent with its having a role in deprotocupration-aroylation. Phenyl pyridyl ketones, phenyl quinolyl ketones, and phenyl thienyl ketones were prepared in tetrahydrofuran using the lithiocuprate and aroyl chorides as electrophiles. Diaryl ketones bearing a chloro group at the 2 position (of a pyridyl or phenyl group) thus synthesized were next converted through palladium-catalyzed ring closure to polycycles of the 5H-indeno[1,2-b]pyridin-5-one, 11H-indeno[1,2-b]quinolin-11-one, 9H-indeno[2,1-c]pyridin-9-one, and 8H-indeno[2,1-b]thiophen-8-one families. (C) 2013 Elsevier Ltd. All rights reserved.

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