A Simple Precursor for Highly Functionalized Fused Imidazo[4,5-b]pyridines and Imidazo[4,5-b]-1,8-naphthyridine

Al-Duaij, Omar K.; Zaki, Magdi E. A.; Gazzar, Abdel-Rhman B. A. El

doi:10.3390/molecules21121646

Cited by 6 publications

(2 citation statements)

References 27 publications

(33 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Al-duaij et al [ 86 ] described an interesting method of imidazo[4,5- b ]pyridine synthesis using malononitrile. First, heating diaminomaleonitrile 41 with triethyl orthoformate in dioxane afforded ethyl [2-amino-1,2-dicyanovinyl]imidoformate 42 .…”

Section: Synthetic Routes To Imidazo[45- B ]Pymentioning

confidence: 99%

“…Next 1-aryl-5-amino-4-(cyanoformimidoyl)imidazoles 44 were reacted with malononitrile under mild experimental conditions and led to 3-aryl-5,7-diamino-6-cyano-3 H -imidazo[4,5- b ]pyridines 45 , when the reaction was carried out in the presence of DBU, or to 3-aryl-5-amino-6,7-dicyano-3 H -imidazo[4,5- b ]pyridines 46 , in its absence. Both reactions evolved from the adduct formed by a nucleophilic attack of the malononitrile anion to the carbon of the cyanoformimidoyl substituent ( Scheme 10 ) [ 86 , 87 ].…”

Section: Synthetic Routes To Imidazo[45- B ]Pymentioning

confidence: 99%

See 1 more Smart Citation

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

2017

View full text Add to dashboard Cite

The structural resemblance between the fused imidazopyridine heterocyclic ring system and purines has prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The discovery of their first bioactivity as GABAA receptor positive allosteric modulators divulged their medicinal potential. Proton pump inhibitors, aromatase inhibitors, and NSAIDs were also found in this chemical group. Imidazopyridines have the ability to influence many cellular pathways necessary for the proper functioning of cancerous cells, pathogens, components of the immune system, enzymes involved in carbohydrate metabolism, etc. The collective results of biochemical and biophysical properties foregrounded their medicinal significance in central nervous system, digestive system, cancer, inflammation, etc. In recent years, new preparative methods for the synthesis of imidazopyridines using various catalysts have been described. The present manuscript to the best of our knowledge is the complete compilation on the synthesis and medicinal aspects of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines reported from the year 2000 to date, including structure–activity relationships.

show abstract

Section: Synthetic Routes To Imidazo[45- B ]Pymentioning

confidence: 99%

Section: Synthetic Routes To Imidazo[45- B ]Pymentioning

confidence: 99%

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

2017

View full text Add to dashboard Cite

show abstract

Selectivity in domino reaction of ortho-carbonyl azides with malononitrile dimer leading to [1,2,3]triazolo[1,5-a]pyrimidines

Pokhodylo

Shyyka

Tupychak

et al. 2018

Chem Heterocycl Comp

View full text Add to dashboard Cite

Malononitrile dimer as a privileged reactant in design and skeletal diverse synthesis of heterocyclic motifs

Shaabani

Hooshmand

2018

Mol Divers

View full text Add to dashboard Cite

Malononitrile dimer as a precursor reactant has been extensively applied in the diversity-oriented synthesis of various heterocyclic motifs, bis-heterocyclic compounds, fused heterocycle derivatives, bicyclic bridged heterocyclic scaffolds, and highly substituted carbocyclic compounds. These remarkable products were synthesized via various types of reactions, such as cycloaddition, cyclocondensation, cascade/domino/tandem reactions along with multi-component reactions. In addition, the flexibility and high reactivity of malononitrile dimer as a multi-functional reagent and its potential to the preparation of novel beneficial scaffolds as well as biologically active molecules signify it as a suitable building block in total synthesis, medicinal chemistry, and dyes. In the present review, the advances in the chemistry of malononitrile dimer as a potent reagent in organic synthesis have been reported in the past to now.

show abstract

A Simple Precursor for Highly Functionalized Fused Imidazo[4,5-b]pyridines and Imidazo[4,5-b]-1,8-naphthyridine

Cited by 6 publications

References 27 publications

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

Selectivity in domino reaction of ortho-carbonyl azides with malononitrile dimer leading to [1,2,3]triazolo[1,5-a]pyrimidines

Malononitrile dimer as a privileged reactant in design and skeletal diverse synthesis of heterocyclic motifs

Contact Info

Product

Resources

About