16560-43-3Relevant articles and documents
Acid-Mediated Halogen Exchange in Heterocyclic Arenes: A Highly Effective Iodination Method
Wolf, Christian,Tumambac, Gilbert E.,Villalobos, Cristina N.
, p. 1801 - 1804 (2007/10/03)
Heterocyclic arenes including pyridyl, quinolyl, and isoquinolyl chlorides have been converted to their corresponding iodides in good to high yields via acid-mediated nucleophilic halogen exchange with sodium iodide. This procedure avoids the use of transition metals, harsh reaction conditions, and affords highly regioselective halide exchange. Chloride substituents in position 2 and 4 of pyridines and quinolines are readily substituted by iodide in 75-91% and conversion of 1-chloroisoquinoline to its iodide derivative was found to proceed with 90% yield. Positions that are not activated for nucleophilic aromatic substitution proved to be inert to halide exchange. Regioselective chloride/iodide exchange in 4,7-dichloroquinoline hydrochloride gave 7-chloro-4-iodoquinoline, an important precursor of anti-malaria drugs, in almost 90% yield.
Synthesis and reactivity of lithium tri(quinolinyl)magnesates
Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
, p. 8629 - 8640 (2007/10/03)
2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.
Studies on Organometallic Compounds. II. Facile and Convenient Method for the Synthesis of Idoazines through Iododestannation of Trimethylstannylazines
Yamamoto, Yukata,Yanagi, Akihiko
, p. 1731 - 1737 (2007/10/02)
Trimethylsatannyl and bis(trimethylstannyl) derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethylstannyl sodium, which was generated in situ from chlorotrimethylsatannane and sodium.These stannyl derivatives readily underwent iododestannation on treatment with iodine to produce the corresponding iodo and diiodo derivatives of pyridine, quinoline, and isoquinoline, respectively, in good yields.Keywords -trimethylsannylazine; bis(trimethylstannyl)azine; iodoazine; diiodoazine; iododestannation; trimethylstannyl sodium; chlorotrimethylstannane