Synthesis of new quinoline fused heterocycles such as benzo[h]-1,6-naphthyridines and pyrazolo[4,3-c]quinolines

Ghotekar, Bhausaheb K.; Ghagare, Maruti G.; Toche, Raghunath B.; Jachak, Madhukar N.

doi:10.1007/s00706-009-0236-1

Cited by 29 publications

(13 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These functionalized [1,6]-naphthyridines and their benzoheterofused analogues are found in many products of marine origin and possess biological activities, including antiproliferative, 306 HIV-1 integrase inhibition, 307 allosteric inhibition of Aktl and Akt2 308 and selective antagonistic activity for 5-HT4 receptors. 309 Traditionally, the synthesis of naphthyridines was carried out either using expensive catalysts [310][311][312] or multistep syntheses, 313 but these greener protocols can offer a useful alternative to synthetically important organic compounds. Indeed, the synthesis of 1,2-dihydro [1,6]naphthyridine and its derivatives using the aforementioned methodology avoids the use of expensive catalysts, toxic organic solvents, and anhydrous conditions.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

et al. 2013

View full text Add to dashboard Cite

Catalyst-free reactions developed during the last decade and the latest developments in this emerging field are summarized with a focus on catalyst-free reactions in-water and on-water. Various named reactions, multi-component reactions and the synthesis of heterocyclic compounds are discussed including the use of various energy input systems such as microwave- and ultrasound irradiation, among others. Organic chemists and the practitioners of this art both in academia and industry hopefully will continue to design benign methodologies for organic synthesis in aqueous media under catalyst-free conditions by using alternative energy inputs based on fundamental principles.

show abstract

Section: Multicomponent Reactionsmentioning

confidence: 99%

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Functionalized 1,6‐naphthyridines are an important class of organic molecules that have attracted much attention from those in the synthetic and medicinal fields 3. Naphthyridine derivatives are extensively used in various pharmacological functions for their antiproliferative, anticancer, HIV‐1 integrase inhibitor, antithrombotic, FGF Receptor‐1 tyrosin kinase inhibitor, allosteric inhibitor of Akt1 and Akt2, antimalerial, and antifungal properties; they also act as selective antagonists of 5‐HT4 receptors 4–7. Over the years, numerous synthetic methods8, 9 have been developed for the construction of these valuable privileged structures.…”

Section: Introductionmentioning

confidence: 99%

Cubic Perovskite ZnTiO₃ Nanopowder as a Recyclable Heterogeneous Catalyst for the Synthesis of 1,6‐Naphthyridines in Water

et al. 2015

View full text Add to dashboard Cite

Cubic perovskite ZnTiO3 nanopowder has been prepared by means of a sustainable sol–gel method. The nanopowder (12–20 nm) has been thoroughly characterized by N2 sorption analysis, high‐resolution (HR) TEM, X‐ray diffraction (XRD), X‐ray photoelectron spectroscopy (XPS), SEM, and FTIR analyses. The environmentally benign synthesis of highly substituted 1,6‐naphthyridines catalyzed by ZnTiO3 nanopowder in aqueous media has been demonstrated. It requires two different catalytic functions, that is, an acid one, which is provided by TiIV ions, and a basic one, which is provided by the oxide ion incorporated within the ZnTiO3 metal oxide framework. 1,6‐Naphthyridines are of tremendous biological importance, and this method is simple and environmentally friendly. The greenness of the process was satisfactorily established as water was exploited as the reaction medium and there was very high atom economy.

show abstract

“…These compounds show a wide range of pharmacological activities such as antitumor,5a antimicrobial,5b allosteric,5c and antiproliferative activities 5d. In addition, functionalized 1,6‐naphthyridines are well‐known inhibitors of human cytomegalovirus6a and HIV‐1 integrase,6b and are selective antagonists of 5‐HT4 receptors 6c. Due to their immense potential, various research groups have put considerable effort into the synthesis of these compounds in recent times.…”

Section: Introductionmentioning

confidence: 99%

Sodium‐Hydroxide‐Mediated Synthesis of Highly Functionalized [1,6]‐Naphthyridines in a One‐Pot Pseudo Five‐Component Reaction

2013

View full text Add to dashboard Cite

The synthesis of hitherto unreported 5‐amino‐7‐alkoxy‐2‐methyl‐2,4‐aryl‐1,2‐dihydro‐1,6‐naphthyridine‐8‐carbonitriles (4) was accomplished by a one‐pot pseudo five‐component reaction using aryl methyl ketones or alkyl methyl ketones, malononitrile, and alcohols in the presence of sodium hydroxide under reflux conditions. By following an identical reaction procedure, various 5‐amino‐2‐methyl‐2,4‐diaryl‐7‐(arylthio)‐1,2‐dihydro‐1,6‐naphthyridine‐8‐carbonitrile derivatives (6) were also synthesized from aryl methyl ketones, malononitrile, and thiophenols in the presence of sodium hydroxide in ethanol. High bond‐forming efficiency, good yields, and the use of a readily available base are some of the salient features of this multicomponent reaction.

show abstract

Synthesis of new quinoline fused heterocycles such as benzo[h]-1,6-naphthyridines and pyrazolo[4,3-c]quinolines

Cited by 29 publications

References 26 publications

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

Cubic Perovskite ZnTiO₃ Nanopowder as a Recyclable Heterogeneous Catalyst for the Synthesis of 1,6‐Naphthyridines in Water

Sodium‐Hydroxide‐Mediated Synthesis of Highly Functionalized [1,6]‐Naphthyridines in a One‐Pot Pseudo Five‐Component Reaction

Contact Info

Product

Resources

About

Synthesis of new quinoline fused heterocycles such as benzo[h]-1,6-naphthyridines and pyrazolo[4,3-c]quinolines

Cited by 29 publications

References 26 publications

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis

Cubic Perovskite ZnTiO3 Nanopowder as a Recyclable Heterogeneous Catalyst for the Synthesis of 1,6‐Naphthyridines in Water

Sodium‐Hydroxide‐Mediated Synthesis of Highly Functionalized [1,6]‐Naphthyridines in a One‐Pot Pseudo Five‐Component Reaction

Contact Info

Product

Resources

About

Cubic Perovskite ZnTiO₃ Nanopowder as a Recyclable Heterogeneous Catalyst for the Synthesis of 1,6‐Naphthyridines in Water