290. The nitration of some simple heterocyclic nitrogen compounds

Schofield, K.; Swain, Trilochan

doi:10.1039/jr9490001367

Cited by 15 publications

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“…It was found that the color and crystalline form of 8-amino-4-methylcinnoline (III) is identical with that described in the literature (3) but the melting point is 133-134°, compared to the literature value of 126-127°. The structure of III was proved therefore by the conversion of it via the Sandmeyer reaction to 8-chloro-4-methylcinnoline (IV), a yellow crystalline product melting at 124-125°( m.p.…”

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The Synthesis of some Substituted Pyrido[3,2-h]Cinnolines

Mckenzie¹,

Hamilton²

1951

J. Org. Chem.

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One of the methods of producing an N-heterocyclic ring involves the condensation of ethoxymethylenemalonate with a primary amine and subsequent ring closure. This method has been employed with 8-amino-4-methylcinnoline in the synthesis of substituted pyrido[3,2-Zi]cinnolines.4-Methylcinnoline (I) was prepared, in good yield, according to the directions of Jacobs, et al. (1). Nitration of I (2) gave 4-methyl-8-nitrocinnoline (II).Reduction of II was accomplished by three different methods: A. Stannous chloride and hydrochloric acid (3); B. "Etched" iron and aqueous ethanol (4); C. Raney nickel and hydrogen at 45 pounds pressure. The best yields were obtained using the stannous chloride procedure; however, the ease of isolating the product made the "etched" iron method preferable when large amounts of nitro compound were used. SUMMARY 1. The synthesis of several substituted pyrido[3,2-A]cinnolines is reported.2. The ultraviolet spectrum of three cinnoline derivatives in ethanol solution is given.

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“…8-Amino-4-methylcinnolme (III). The procedure giving the best yield was the stannous chloride method described by Schofield and Swain (3). The product when recrystallized from benzene gave a 70% yield of orange crystals, m.p.…”

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The Synthesis of some Substituted Pyrido[3,2-h]Cinnolines

Mckenzie¹,

Hamilton²

1951

J. Org. Chem.

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“…The substituted benzoic acids were 0021 -9568/83/1728-0428$01.50/0 © 1983 American Chemical Society °Elemental analyses for C, H, and N in agreement with theoretical values were obtained and submitted for review. 6 Reported mp: [160][161] (2), 149 (4). c Reported mp: 145-146 (4).…”

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confidence: 99%

Syntheses of 1-phenyl-2-(3,4-dihydro-4-quinazolinylidene)ethanone and related ethanones

Sund¹,

Beall²,

Borgfeld³

1983

J. Chem. Eng. Data

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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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290. The nitration of some simple heterocyclic nitrogen compounds

Cited by 15 publications

References 0 publications

The Synthesis of some Substituted Pyrido[3,2-h]Cinnolines

The Synthesis of some Substituted Pyrido[3,2-h]Cinnolines

Syntheses of 1-phenyl-2-(3,4-dihydro-4-quinazolinylidene)ethanone and related ethanones

The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

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