869301-30-4Relevant academic research and scientific papers
A convenient alumination of functionalized aromatics by using the frustrated Lewis pair Et3Al and TMPMgCl·LiCl
Unsinn, Andreas,Wunderlich, Stefan H.,Jana, Anukul,Karaghiosoff, Konstantin,Knochel, Paul
, p. 14687 - 14696 (2013)
A straightforward and efficient alumination of functionalized arenes by using the frustrated Lewis pair Et3Al and TMPMgCl×LiCl (TMP=2,2,6,6-tetramethylpiperidyl) has been developed. In particular, halogenated electron-rich aromatics can be smoothly functionalized by using the frustrated Lewis pair Et3Al and TMPMgCl×LiCl. Compared with previously described alumination methods, this procedure avoids extensive cooling and the need for an excess of base. This in situ procedure has proven to be most practical and allows for regio- and chemoselective metalation of a wide range of aromatics with sensitive functional groups (CONEt2, CO 2Me, CN, OCONMe2) or halogens (F, Cl, Br, I). The resulting aromatic aluminates, which were characterized by using NMR spectroscopy, were subjected to allylations, acylations, and palladium-catalyzed cross-coupling reactions after transmetalation to zinc. It was shown that the nature of the Zn salt used for transmetalation is crucial. Thus, compared with ZnCl2 (2equiv), the use of Zn(OPiv)2 (2equiv; OPiv=pivalate) allows the subsequent quenching reactions to be performed with only a slight excess of electrophile (1.2equiv) and provides interesting functionalized aromatics in good yields.
Synthesis of 1-aminonaphthalene-2-carbonitrile derivatives by the reaction of 2-vinylbenzonitriles with 2-lithioacetonitrile
Kobayashi, Kazuhiro,Hashimoto, Kenichi,Ukon, Takahiro,Fukamachi, Shuhei,Morikawa, Osamu,Konishi, Hisatoshi
, p. 584 - 588 (2008/12/22)
A new and simple method for the preparation of 1-aminonaphthalene-2- carbonitrile derivatives has been developed. When 2-(1-arylethenyl)benzonitriles are treated with 2-lithioacetonitrile, 1-amino-4-aryl-3,4-dihydronaphthalene-2- carbonitriles are obtained in good yields. The reaction of 2-(1-aryl-2- methoxyethenyl)benzonitriles with 2-lithioacetonitrile leads to the formation of 1-amino-4-arylnaphthalene-2-carbonitriles in fair-to-good yields. Georg Thieme Verlag Stuttgart.
DIPHENYLMETHANE DERIVATIVES AS INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS
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Page/Page column 47; 48, (2008/06/13)
The instant invention provides compounds of Formula I which are 5-lipoxygenase activating protein inhibitors. Compounds of Formula I are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.
