Add time:07/25/2019         Source:sciencedirect.com

Publisher SummaryThis chapter presents the reactions leading to the benzo[c]cinnoline ring system. The chapter discusses the cyclization reactions of biphenyl derivatives including 2-substituted biphenyls. In these reactions when certain derivatives of 2-aminobiphenyl, having activating substituents in the other ring, are diazotized, they undergo internal coupling to give benzo[c]cinnolines; 2,2′-disubstituted biphenyls. The most widely used method for forming the benzo[c]cinnoline nucleus is the reduction of 2,2′-dinitrobiphenyl and its derivatives under alkaline conditions, analogous to the bimolecular reduction of nitroarenes. The action of nitrous acid on dibenzo[c,e][1,2]azaborines is also discussed. The chapter discusses the cyclization of azobenzenes including thermal and photochemical reactions. The photochemical bridging and subsequent ring cleavage of tetrazolium salts is also reviewed. The chapter also illustrates the ring contraction of other heterocycles, such as diazepines, triazepines, and thiadiazepines. Benzo[c]cinnoline is a weekly basic compound; it is very soluble in alcohols and ether. The other physical properties of benzo[c]cinnoline such as ultraviolet spectrum, nuclear magnetic resonance spectrum, and mass spectrum are presented.

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