Transformation of 4-oxo-4H-[1]-benzopyran-3-carboxaldehydes into pyrazolo[3,4-b]pyridines

doi:10.1002/JHET.5570430405

Paper

Transformation of 4-oxo-4H-[1]-benzopyran-3-carboxaldehydes into pyrazolo[3,4-b]pyridines

Published Jul 1, 2006 · H. Stankovičová, A. Gáplovský, M. Lácová

Journal of Heterocyclic Chemistry

Q3 SJR score

8

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Reaction of 6-methyl-4-oxo-4H-[1]-benzopyran-3-carboxaldehyde 1 with 5-amino-3-methyl-1-phenylpyrazole 2 in alcoholic reaction media in the presence of 4-toluenesulfonic acid as catalyst afforded 5-(2-hydroxy-5-methylbenzoyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine 3 and 2-methoxy-6-methyl-3-(3-methyl-1-phenylpyrazol-5-ylaminomethylene)chroman-4-one 7. We explain the mechanism of formation of both products on the basis of kinetic study of individual reaction steps.

Study Snapshot

Reaction of 6-methyl-4-oxo-4H-[1]-benzopyran-3-carboxaldehyde with 5-amino-3-methyl-1-phenylpyrazole in alcoholic media with 4-toluenesulfonic acid produces 5-(2-hydroxy-5-methyl

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Transformation of 4-oxo-4H-[1]-benzopyran-3-carboxaldehydes into pyrazolo[3,4-b]pyridines

Sign up to use Study Snapshot

References

Reaction of 3-formylchromones with aromatic amino carboxylic acids

Acid catalyzed reaction of 3-formylchromones with aromatic amino carboxylic acids in alcoholic media produces 3-(aryliminomethyl)chromones, while dry aprotic media yields 2-hydroxy-3-(arylaminomethylene)chroman-4-ones.

Synthesis and Theoretical Study of Mannich Type Reaction Products of 3-Formylchromones with Triazoles and Amides and Nucleophilic Formation of 2,3-Disubstituted-4-Chromanones

The semiempirical PM3 method enables the study of reaction paths and optimal structures in Mannich type reactions, leading to the synthesis of various compounds with confirmed structures.

Pyrazolo[3,4-b]pyridines: Syntheses, reactions, and nuclear magnetic resonance spectra

2-Chloro-3-formylpyridine can be synthesized through reduction of 2-chloro-3-cyanopyridine, but yield is affected by azine species formation.

The synthesis of pyridine derivatives from 3‐formylchromone

3-formylchromone reacts with active methylene derivatives to produce pyridine derivatives, and enamine derivatives can yield pyrido compounds in one step.

Heterocyclic synthesis with β‐ketosulfoxides IV. Synthesis of 3‐substituted chromones

This novel synthesis of 3-(hydroxymethyl)chromones from o-hydroxy--(methylsulfinyl)acetophenones allows for the synthesis of 3-formyl, 3-cyano, 3-carboxy, 3-carboxamido, 3-chloromethyl, 3-

Chromon‐3‐carbaldehyde

Chromone-3-carbaldehyde is a general-purpose reaction for preparing cationic dyes 5a and 5b, with potential applications in organic synthesis and pharmaceuticals.

The reactions of 2,2‐difluoro‐4‐methylnaphtho[l,2‐e]‐1,3,2‐dioxaborin and its [2,1‐e]isomer with N,N‐dimethylformamide

The [2,1-e] isomer of 2,2difluoro-4methylnaphtho[l,2e]-1,3,2dioxaborin reacts with N,N-dimethylformamide to produce benzochroman-4-ones,

Citations

Synthesis, reactions and antineoplastic activity of 3-(2-oxo-2H-chromen-3-yl)-2-oxo-2H,5H-pyrano[3,2-c]chromene derivatives

3-(2-oxo-2H-chromen-3-yl)-2H,5H-pyrano[3,2-c]chromen-2-one shows promising antitumor activity, warranting further study.

Regioisomeric 4-amino- and 6-aminopyrazolo[3,4-b]pyridines: synthesis and structure determination by NMR spectroscopy and X-ray diffraction

Selective synthesis of regioisomeric 4-amino- and 6-aminopyrazolo[3,4-b]pyridines was developed, yielding quantitative yields and demonstrating their spectral differences using 13C NMR spectra.

A facile route to phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes

This study presents a facile route to phenyl, phenylsulfanyl, and phenylselanyl substituted pyrano[3,2-c]chromenes through cyclocondensation of 4-oxo-4H-chromen-3-carbald

Convenient synthesis and unusual reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes

The study demonstrates a convenient synthesis and unusual reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes in water, alcohol, and acetic acid under Perkin conditions.