Cinnoline Chemistry. I. Some Condensation Reactions of 4-Chlorocinnoline

An efficient synthesis of 4-benzyl cinnolines from aryl phenylallylidene hydrazone is described. In this report aluminium chloride as a Lewis acid catalyst and toluene as a solvent are used for the synthesis. This method is expected to more advantageous than the other reported methods of synthesis of the cinnoline rings because of its low cost, better yield, and benign reaction conditions.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications ® for the following free supplemental resource(s): Full experimental and spectral details.]

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“…[24] 104.5°C); IR υ/(KBr) cm −1 : 3089 cm −1 (Ar-H), 2846 cm −1 (C-H), 1592 cm −1 (N=N), 1280 cm −1 (-C-N=N), 1195 cm −1 (-N=N-C). 1 …”

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Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones

Gogoi

Devi

et al. 2014

Synthetic Communications

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The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Parmerter

2011

Organic Reactions

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A diazonium salt will couple with an aliphatic compound containing an activated carbon‐hydrogen bond. This discussion is limited to those reactions in which both the nitrogen atoms of the diazonium salts are retained in the resulting molecule. The discussion is further limited by the exclusion of coupling reactions, which occur with the elimination of a group from an activated methinyl compound, the Japp‐Klingemann reaction. These reactions are discussed in Chapter 2. Much of the early work with coupling was prompted by the desire to determine whether the products were of the azo or hydrazonestructure. It is difficult to establish the structures in such cases where the tautomeric forms are possible. It is generally considered that the hydrazone is the stable form.

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Cinnolines

Singerman¹

1973

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Cinnoline Chemistry. I. Some Condensation Reactions of 4-Chlorocinnoline

Cited by 8 publications

References 3 publications

Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones

Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones

The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Cinnolines

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