Metalation, directed, of pyridines quinolines, and diazines

Mass spectral techniques in heterocyclic chemistry applications and stereochemical considerations in carbohydrates and other oxygen heterocycles, 42, 335 Mass spectrometry of heterocyclic compunds, 7, 301 of nucleic acids, 39, 79 Medium-large and large 7r-excessive heteroannulenes, 23, 55 Meso-ionic compounds, 19, 1 Metal catalysts, action on pyridines, 2, 179 Metalation, directed, of pyridines, quinolines, and diazines, 52, 187... 

Queguiner, G., Marsais, F., Snieckus, V., Epsztajn, J., Directed Metalation of n-Deficient Azaaromatics Strategies of Functionalization of Pyridines, Quinolines, and Diazines, 52, 187. 

Directed metalation of -deficient azaaromatics strategies of functionalization of pyridines, quinolines, and diazines, 52, 187 gem-Dithienylalkanes and their derivatives, 32, 83... 

Directed metallation of pyridines, quinolines, and diazines 91AHC (52)187. 

Heteroatom-facilitated lithiations , Gschwend, H. W. and Rodriguez, H. R., Org. React., 1979, 26, 1 Directed metallation of 7r-deficient azaaromatics strategies of functionalisation of pyridines, quinolines, and diazines , Queguiner, G., Marsais, F., Snieckus, V., and Epsztajn, J., Adv. Heterocycl. Chem., 1991, 52, 187 Metallation and metal-assisted bond formation in 7r-electron deficient heterocycles , Undheim, K. and Benneche, T., Heterocycles, 1990, 30, 1155 Directed ortho metallation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics , Snieckus, V., Chem. Rev., 1990, 90, 879. 

Mongin, F., Queguiner, G. Advances in the directed metallation of azines and diazines (pyridines, pyrimidines, pyrazines, pyridazines, quinolines, benzodiazines and carbolines). Part 1 Metallation of pyridines, quinolines and carbolines. Tetrahedron 2001, 57,4059-4090. 

The direct metalation of 5-methylpyrimidine and 5,5 -bipyrimidinyl in the 4-position has been reported with LDA in low yield [74TL2373 75AG(E)713], but apart from that there are few other reports on the direct metalation of unactivated diazines. However, as with pyridine and quinoline, directed metalation can readily be achieved with all three of the diazine systems when the appropriate substituent groups are present [91AHC(52)187]. Thus, the direct lithiation of pyridazine in the 4-position has now been achieved with both the 3,6-dichloro and the... 

The direct introduction of an acetylide moiety, using pyridine A-oxide (or quinoline, diazine and triazine iV-oxides) can be achieved in a comparable way, by reaction with potassium phenylacetylide reaction with the lithium salt requires addition of acetyl chloride at the end of the reaction to aromatise. At low temperature, and using i-PrMgCl, 2-metallation of pyridine iV-oxides can be achieved, and thus, the introduction of electrophiles at the 2-position. ... 

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