Synthesis of Pyrido[4,3-b]quinoline (2,10-Diazaanthracene) and Related Compounds

Coscia, Anthony T.; Dickerman, S. Carlton

doi:10.1021/ja01521a046

Cited by 14 publications

(3 citation statements)

References 1 publication

(1 reference statement)

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“…Pure product (14.1 g, 89%) was obtained as yellow needles of mp 339-341 °C dec. Quoted melting points for this product, from various routes, are 339 °C dec20 and 338-339 °C dec. 26 corresponding azaacridone in either S0C12 or POCl3 necessitates use of a solvent in conversion to the chloro compound. A sample of the 2-azaaeridone (1 g, 5.1 mM) was suspended in pyridine (10 mL) and the mixture boiled and stirred until a solution resulted.…”

Section: Methodsmentioning

confidence: 99%

Potential antitumor agents. 25. Azalogs of the 4'-(9-acridinylamino)methanesulfonanilides

Denny¹,

Atwell²,

Cain³

1977

J. Med. Chem.

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Tumor inhibition inhibition produced by isomeric, nitro-substituted 4'-(9-acridinylamino)methanesulfonanilide analogues of low base strength (pKa=4.79-5.72) might result from in vivo reduction to the corresponding, higher pKa (7.15-9.80), tumor active amines. The aza analogues,-N=in place of -C(NO2)=, have been prepared as nonclassical bioisosteres and screened in the L1210 system. Significant L1210 inhibition produced by isomeric 3- and 4-azalogues, of similar base strength to the corresponding nitro-substituted derivatives, demonstrates that weakly basic analogues can provide biologic activity when there is no prospect of in vivo reduction to more strongly basic products. Obligatory reduction of nitro function, for biologic activity, need not be postulated in this drug series.

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Section: Methodsmentioning

confidence: 99%

Potential antitumor agents. 25. Azalogs of the 4'-(9-acridinylamino)methanesulfonanilides

Denny¹,

Atwell²,

Cain³

1977

J. Med. Chem.

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“…However, their benzo analogues have been less explored. Coscia et al have reported the first synthesis of the parent compound from aniline and 1-acetyl-3-ethoxycarbonyl-4-piperidone by condensation and dehydrogenation reactions . Recently, the groups of Verma and Langer have reported silver-catalyzed tricyclic/tetracyclic benzo[ b ][1,6]naphthyridines via multicomponent reactions from 2-alkynylquinoline-3-carbaldehydes, respectively.…”

Section: Introductionmentioning

confidence: 99%

Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]naphthyridines from 2-Chloroquinoline-3-carbonitriles Using Sulfur and Amines As Nucleophiles

2017

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A palladium-catalyzed one-pot stepwise coupling-annulation reaction of 2-chloroqunoline-3-carbonitriles enabled the direct synthesis of sulfur-substituted benzo[b][1,6]naphthyridines via multiple bond formation. The reaction provided an unusual mode for cyclization as sodium sulfide, a soft nucleophile, preferred to attack on the carbon of the nitrile group rather than on the C-C triple bond. The developed chemistry was extended with the secondary amines as nucleophiles to afford nitrogen-substituted benzo[b][1,6]naphythyridines while primary amines afforded hydroamination products . The hydromination products were transformed to benzo[b][1,6]naphthyridones via a base-mediated cyclization reaction. The developed protocol features inexpensive and easily synthesizable starting materials, easy operations, and a high efficiency and tolerance to a broad range of substrates.

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“…and Related Compounds a. thiones To our knowledge, during the last fewr years very few thiones have been desulfurized; 3-thiono-4-cholestene (CXXXVII), when refluxed in dioxane with Raney nickel, gave 4-cholestene in unstated yield (85).Thioacridone (CXXXVIII) yielded a maximum of 25% of acridine, and desulfurization of pyrido[4,3-b ]quinolin-10(5H)-thione (CXXXIX) was accompanied by extensive reduction of the ring system(123).…”

mentioning

confidence: 99%

The Action of Raney Nickel on Organic Sulfur Compounds.

Hauptmann¹,

Walter²

1962

Chem. Rev.

127

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Synthesis of Pyrido[4,3-b]quinoline (2,10-Diazaanthracene) and Related Compounds

Cited by 14 publications

References 1 publication

Potential antitumor agents. 25. Azalogs of the 4'-(9-acridinylamino)methanesulfonanilides

Potential antitumor agents. 25. Azalogs of the 4'-(9-acridinylamino)methanesulfonanilides

Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]naphthyridines from 2-Chloroquinoline-3-carbonitriles Using Sulfur and Amines As Nucleophiles

The Action of Raney Nickel on Organic Sulfur Compounds.

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