ChemInform Abstract: Ultrasonically Accelerated Vilsmeier Haack Cyclization and Formylation Reactions.

Ali, M. M.; Sana, Sariah; Tasneem, Tasneem; Rajanna, K. C.; Saiprakash, P. K.

doi:10.1002/chin.200236047

Cited by 4 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…192 The mechanism of the Meth-Cohn quinoline synthesis involves the initial conversion of the acetanilide into a tautomeric R-iminochloride/R-chloroenamine mixture by the action of POCl 3 , which is subsequently C-formylated by the Vilsmeier reagent derived from POCl 3 and DMF, followed by a second formylation, cyclization, and aromatization by loss of dimethylamine to give the final 2-chloro-3-quinoline carboxaldehyde. 191 The reaction can be accelerated in micellar media 193 by ultrasound 194 and microwave irradiation. An alternative reverse Vilsmeier strategy is known involving ring closure of the Vilsmeier reagents derived from N-aryl-N-methylformamides with electron-rich olefins.…”

Section: Comparison To Other Methodsmentioning

confidence: 99%

Recent Advances in the Friedländer Reaction

et al. 2009

View full text Add to dashboard Cite

Section: Comparison To Other Methodsmentioning

confidence: 99%

Recent Advances in the Friedländer Reaction

et al. 2009

View full text Add to dashboard Cite

“…Unfortunately, no desired product could be isolated by increasing the temperature or the equivalents of DMF and/or phosphorus oxychloride. Furthermore, activation of the reaction by sonication at lower temperature or by using acetonitrile (ACN) and/or sodium dodecyl sulfate (SDS) as additives according to the protocols of Ali et al remained unsuccessful [30,31].…”

Section: Chemistrymentioning

confidence: 99%

Novel Radioiodinated and Radiofluorinated Analogues of FT-2102 for SPECT or PET Imaging of mIDH1 Mutant Tumours

et al. 2022

View full text Add to dashboard Cite

Isocitrate dehydrogenases (IDHs) are metabolic enzymes commonly mutated in human cancers (glioma, acute myeloid leukaemia, chondrosarcoma, and intrahepatic cholangiocarcinoma). These mutated variants of IDH (mIDH) acquire a neomorphic activity, namely, conversion of α-ketoglutarate to the oncometabolite D-2-hydroxyglutarate involved in tumourigenesis. Thus, mIDHs have emerged as highly promising therapeutic targets, and several mIDH specific inhibitors have been developed. However, the evaluation of mIDH status, currently performed by biopsy, is essential for patient stratification and thus treatment and follow-up. We report herein the development of new radioiodinated and radiofluorinated analogues of olutasidenib (FT-2102) as tools for noninvasive single photon emission computed tomography (SPECT) or positron emission tomography (PET) imaging of mIDH1 up- and dysregulation in tumours. Nonradiolabelled derivatives 2 and 3 halogenated at position 6 of the quinolinone scaffold were synthesised and tested in vitro for their inhibitory potencies and selectivities in comparison with the lead compound FT-2102. Using a common organotin precursor, (S)-[125I]2 and (S)-[18F]3 were efficiently synthesised by radio-iododemetallation and copper-mediated radiofluorination, respectively. Both radiotracers were stable at room temperature in saline or DPBS solution and at 37 °C in mouse serum, allowing future planning of their in vitro and in vivo evaluations in glioma and chondrosarcoma models.

show abstract

“…Other similar formylating agents, such as DMF-dimethyl acetal, have been used as variants of the Vilsmeier-Haack reagent [253] . Recently, the synthesis of 3formylchromones by the Vilsmeier-Haack reaction was improved using microwave and solid-supported methods [254,255] .…”

Section: + + Scheme 24 Synthesis Of Chromones Viamentioning

confidence: 99%

Chromone: A Valid Scaffold in Medicinal Chemistry

et al. 2014

View full text Add to dashboard Cite

The last few decades have provided stunning progresses in the understanding of physiopathology of several diseases. The remarkable progress in research fields, like genetics, immunology, neurobiology, among others, as well as the advent of more powerful tools, have made it possible to characterize, monitor, and understand far more of the basis of physiology and disease. However, for some diseases the treatment remains a problematic issue as the efforts performed so far were not translated into therapeutic solutions. Notwithstanding the steady increase in the total amount of FCUP

show abstract

ChemInform Abstract: Ultrasonically Accelerated Vilsmeier Haack Cyclization and Formylation Reactions.

Cited by 4 publications

References 1 publication

Recent Advances in the Friedländer Reaction

Recent Advances in the Friedländer Reaction

Novel Radioiodinated and Radiofluorinated Analogues of FT-2102 for SPECT or PET Imaging of mIDH1 Mutant Tumours

Chromone: A Valid Scaffold in Medicinal Chemistry

Contact Info

Product

Resources

About