Cinnoline Research Articles

Understanding the aqueous chemistry of quinoline and the diazanaphthalenes: insight from DFT study

The inter-fragment interactions at various binding sites and the overall cluster stability of quinolone (QNOL), cinnoline (CNOL), quinazoline (QNAZ), and quinoxaline (QNOX) complexes with H2O were studied using the density functional theory (DFT) approach. The adsorption and H-bond binding energies, and the energy decomposition mechanism was considered to determine the relative stabilization status of the studied clusters. Scanning tunneling microscopy (STM), natural bonding orbitals (NBO) and charge decomposition were studied to expose the electronic distribution and interaction between fragments. The feasibility of formations of the various complexes were also studied by considering their thermodynamic properties. Results from adsorption studies confirmed the actual adsorption of H2O molecules on the various binding sites studied, with QNOX clusters exhibiting the best adsorptions. Charge decomposition analysis (CDA) revealed significant charge transfer from substrate to H2O fragment in most complexes, except in QNOL, CNOL and QNAZ clusters with H2O at binding position 4, where much charges are back-donated to substrate. The O---H inter-fragment bonds was discovered to be stronger than counterpart N---H bonds in the complexes, whilst polarity indices confirmed N---H as more polar covalent than O---H bonds. Thermodynamic considerations revealed that the formation process of all studied complexes are endothermic (+ve ΔHf) and non-spontaneous (+ve ΔGf).

Investigations of a Novel Process to the Framework of Benzo[c]cinnoline.

For Abstract see ChemInform Abstract in Full Text.

On The Chemistry of Cinnoline IV [1]. Synthesis and Reactions of (4-Aminocinnolin-3-yl)-aryl-methanones

On The Chemistry of Cinnoline IV [1]. Synthesis and Reactions of (4-Aminocinnolin-3-yl)-aryl-methanones

Synthesis of Fluorobenzo[c]Cinnolines

Abstract The synthesis of 1-, 2-, 3- and 4-monofluoro, and 3,8-difluoro-benzo[c]cinnolines were described.

Effect of sintering the Vycor supports on the surface-induced transformations of embedded benzo[c]cinnoline

Effect of sintering the Vycor supports on the surface-induced transformations of embedded benzo[c]cinnoline

The Photochemical Reaction of Benzo[c]cinnoline. IV. Comments on the Mechanism of 2,2′-Diaminobiphenyl Formation

Abstract In order to determine the mechanism of 2,2′-diaminobiphenyl formation from benzo[c]cinnoline, effect of aldehyde on the reaction was examined. It is proposed that ethanal, which was generated from ethanol in the initial photoreduction, formed an adduct with 5,6-dihydrobenzo[c]cinnoline, and that the resulting adduct participated in the subsequent photo-induced 2,2′-diaminobiphenyl formation.

Intramolecular 1,1-cycloaddition of nitrilimines as a route to benzodiazepines and cyclopropa[c]cinnolines

Intramolecular 1,1-cycloaddition of nitrilimines as a route to benzodiazepines and cyclopropa[c]cinnolines

Cycloaddition of benzocinnoline N-acylimides to diphenylketen

Benzo[c]cinnoline N-acylimides (1) give the rearranged adducts (2) with diphenylketen; the ylide (6) can be intercepted in this reaction suggesting that the expected 1,3-diplor cycloadduct (5) is formed initially and rearranges to (2) both intramolecularly and by dissociation-recombination.

1H-benzo[de]cinnoline and 8-hydroxy-1-naphthonitrile

8-Hydroxy-1-naphthaldehyde reacts with hydrazine to give 1H-benzo[de]cinnoline; some reduction to 8-methyl-1-naphthol also takes place. The oxime of 8-hydroxy-1-naphthaldehyde does not cyclise analogously to an oxazine; instead dehydration to the nitrile occurs.

Electroorganic Preparations. XXIII. Polarography and Reduction of Cinnoline and Related Compounds.

Electroorganic Preparations. XXIII. Polarography and Reduction of Cinnoline and Related Compounds.

248. Benzo[c]cinnolines. Part II. The synthesis and reactions of some benzo[c]cinnoline oxides

248. Benzo[c]cinnolines. Part II. The synthesis and reactions of some benzo[c]cinnoline oxides

Photochemical Reactions of Azo Compounds. II. Photochemical Cyclodehydrogenations of Methyl- and Dimethylazobenzenes

Substituted benzo[c]cinnolines have been prepared from substituted azobenzenes by photochemical cyclodehydrogenation in 22N sulphuric acid. The reaction seems to involve a photochemical disproportionation as rearrangement products of the corresponding hydrazobenzenes were also formed. 4-Methylazobenzene gave 2-methylbenzo[c]cinnoline. 3-Methylazobenzene gave a mixture of 1- and 3-methylbenzo[c]cinnolines: and 2-methylazobenzene gave 4-methylbenzo[c]cinnoline and benzo[c]cinnoline. The latter result is noteworthy as it indicates that cyclization can proceed with elimination of a methyl substituent. Similar elimination was observed with 2,2'-dimethylazobenzene, which gave 4-methyl-benzo[c]cinnoline as well as the expected 4,7-dimethylbenzo[c]cinnoline. Photochemical cyclodehydrogenations of 4,4'-dimethylazobenzene and of 3,3'-dimethyl-azobenzene have also been studied.

Synthesis of Cinnoline N-Oxides

Synthesis of Cinnoline N-Oxides

Cinnoline Chemistry. II. The Condensation of 4-Methylcinnoline with Aldehydes

Cinnoline Chemistry. II. The Condensation of 4-Methylcinnoline with Aldehydes

575. Cinnolines. Part XXIX. 8-Hydroxycinnoline and some of its derivatives

575. Cinnolines. Part XXIX. 8-Hydroxycinnoline and some of its derivatives

506. Cinnolines. Part XXII. Experiments in the indane and tetralin series. Some new 4-hydroxycinnolines

506. Cinnolines. Part XXII. Experiments in the indane and tetralin series. Some new 4-hydroxycinnolines

348. Cinnolines. Part XIX. The preparation and reactions of some 8-nitro-4-hydroxy-and 4-hydroxyBz-methyl-cinnolines

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4-Substituted Cinnoline Derivatives1

4-Substituted Cinnoline Derivatives¹