Borsche cinnoline synthesis

Borsche cinnoline synthesis 141 Bromo-de-diazoniation 194, 230ff., 270, 301... 

See the Borsche Cinnoline Synthesis and the von Richter Cinnoline Synthesis for other preparations of cinnolines. 

Bart Reaction Borsche (Cinnoline) Synthesis Demianov Rearranement Diazo Reaction Gattermann Reaction Gattermann Method Pschorr Arvlation Sandmever Reaction Schiemann Reaction (Bak-Schiemann JRxn) Tiffeneau-Demianov Reaction fVidman-Stoermer ([Pg.847]

A deficiency of the Borsche cinnoline synthesis lies in the fact that the orthoacyl aniline starting materials are sometimes not available by convenient means. In the older literature, the starting materials were prepared by the nitration of acetophenones, followed by a difficult separation of the ortho-and meta-nxiro isomers, followed last by reduction of the nitro group to afford the aniline. ... 

More recently, a cinnoline containing inhibitor of protein kinase B (13) has been prepared through the use of the Borsche cinnoline synthesis. The origin of this product in the Borsche synthesis may not be immediately apparent, because there is no functional group at the 4-position of the cinnoline. In this case, the l/f-4-cinnolone product 11 of the Borsche synthesis was reduced to afford the desired intermediate 6-bromocinnoline 12, which was subjected to a Stille coupling to afford 13. 

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