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201. Reissert compound studies. XXI. Arylation reactions

Author

Robert M. Piccirilli and Frank D. Popp

Subjects
chemistry.chemical_compound, chemistry, Organic Chemistry, Quinoline, Nitro, Organic chemistry, General Chemistry, Isoquinoline, Catalysis
Abstract

The anions derived from both the isoquinoline and the quinoline Reissert compounds have been arylated by use of nitro and dinitro arylhalides. p-Fluorobenzaldehyde reacts preferentially at the carbonyl group and does not lead to arylation.

Published
1969
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204. Reaction of 6,7-dimethoxy-3-isochromanone with hydrazine

Author

Frank D. Popp and Gerald M. Rosen

Subjects
chemistry.chemical_compound, chemistry, Organic Chemistry, Hydrazine, chemistry.chemical_element, Organic chemistry, General Chemistry, Alkylation, Hydrazide, Nitrogen, Oxygen, Catalysis
Abstract

The reaction of the title compound with hydrazine resulted in the formation of the hydroxy hydrazide 5. Alkylation of 5 took place on both oxygen and nitrogen. Compound 5 can be reconverted to the title compound or to the corresponding isoquinolone.

Published
1969
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216. Reissert compound studies. XVII. Phosphorus-containing reissert compound analogues

Author

David M. Spatz and Frank D. Popp

Subjects
chemistry.chemical_classification, Base (chemistry), Potassium, Phosphorus containing, fungi, Organic Chemistry, food and beverages, chemistry.chemical_element, Alkylation, Hydrolysis, chemistry.chemical_compound, chemistry, Organic chemistry, Isoquinoline
Abstract

The reaction of isoquinoline, potassium cyamide, and chlorophosphates or chlorothiophosphates leads to the formation of phosphorus containing analogues of Reisert compounds. These analogues can be converted by base to an anion which undergoes elimination to isoquinaldonitrile or which can be alkylated. Acid-catalysed hydrolysis of the analogues leads to isoquinoline.

Published
1968
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220. Azasteroids. v. approaches to the 14,16-diazasteroidal ring system

Author

Lawrence E. Katz and Frank D. Popp

Subjects
Azasteroids, chemistry.chemical_compound, Chemistry, Organic Chemistry, Quinoline, Mineralogy, Ring (chemistry), Medicinal chemistry
Abstract

Making use of Reissert compound II and Reissert compound analogue VI, benzo [f]quinoline has been converted into the 14,16-diazasteroidal ring system. A number of reactions in this ring system are discussed.

Published
1968
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238. ChemInform Abstract: Reissert Compound Studies: The First Pyridine Reissert Compound

Author

Isao Takeuchi, Yoshiki Hamada, Joydeep Kant, and Frank D. Popp

Subjects
chemistry.chemical_compound, Aluminium chloride, Benzoyl chloride, chemistry, organic chemicals, Pyridine, medicine, General Medicine, Methylene, Trimethylsilyl cyanide, Chloride, Medicinal chemistry, medicine.drug
Abstract

Treatment of pyridine with trimethylsilyl cyanide, benzoyl chloride, and aluminium chloride in methylene chloride gave 1-benzoly-2-cyano-1,2-dihydropyridine, providing the first example of a pyridine Reissert compound; several 3-substituted pyridines have also been converted to Reissert compounds.

Published
1988
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241. ChemInform Abstract: The Reaction of N-Carboalkoxy Reissert Analogs with Carboxylic Acids

Author

Frank D. Popp, Barrie C. Uff, and F. F. Duarte

Subjects
chemistry.chemical_classification, Base (chemistry), chemistry, General Medicine, Medicinal chemistry
Abstract

The reaction of N-carboalkoxy Reissert analogs in the presence of carboxylic acids yields the corresponding ester and heterocyclic base. Use of methoxy substituted benzoic acids yields, instead of the ester, the respective anhydride. Amides can also be prepared in a similar fashion.

Published
1988
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248. ChemInform Abstract: NEW COMPOUNDS- ISOQUINOLINE DERIVATIVES AS SIMPLE EMETINE MODELS

Author

R. M. Piccirilli, Frank D. Popp, Raymond F. Watts, and E. O. Snoke

Subjects
chemistry.chemical_compound, chemistry, Simple (abstract algebra), medicine, Emetine, macromolecular substances, General Medicine, Isoquinoline, Combinatorial chemistry, medicine.drug
Abstract

Several new isoquinolines were prepared using Reissert compounds. A few compounds were screened, and they exhibited no antineoplastic activity.

Published
1978
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