[1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole

Dürüst, Yaşar; Sağırlı, Akın; Kariuki, Benson M.; Knight, David W.

doi:10.1016/j.tet.2014.04.083

Cited by 21 publications

(5 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, we have reported some chemistry incorporating mesoionic 1,3-dipoles; namely sydnones, nitrile oxides, nitrile imines and electron-deficient alkenes, alkynes, [22] [21] [10,11] 2-nitromethylenethiazolidine and benzothiophene 1,1-dioxide. [23][24][25][26][27][28] Herein, we report a study of munchnones€ generated from 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids 3 and acetic anhydride, DCC and DIPC in the presence of 2nitromethylenethiazolidine 4 and diisopropylamine.…”

Section: Resultsmentioning

confidence: 99%

Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids

Dürüst

Karakuş

Kariuki

et al. 2018

Synthetic Communications

Self Cite

View full text Add to dashboard Cite

In situ generated 2,4-diaryl substituted munchnones€ from 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido)acetic acids react with acetic anhydride in the presence of 2-nitromethylene thia-zolidine, which is most likely acting as a base, and unexpectedly undergo a Dakin-West type reaction and a concurrent autoxidation reaction leading to the formation of (E)-1-(N,4-dimethylbenzamido)-1-(4fluorophenyl)prop-1-en-2-yl acetate, 4-substitutedphenyl-N-methyl-N-(4-substitutedbenzoyl) benzamides and p-substituted benzoic acids. In addition, a novel and efficient access to N-acyl urea derivatives is described by the reaction between 2-(4-substitutedphenyl)-2-(Nmethyl-N-4-substitutedbenzamido)acetic acids and cyclohexyl, isopropyl carbodiimides in the presence of a base. The structures of all new products were identified on the basis of NMR and IR spectra, along with X-ray diffraction data and HRMS measurements. ARTICLE HISTORY

show abstract

Section: Resultsmentioning

confidence: 99%

Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids

Dürüst

Karakuş

Kariuki

et al. 2018

Synthetic Communications

Self Cite

View full text Add to dashboard Cite

show abstract

“…6-Chloro-9-(prop-2-yn-1-yl)-9 H -purine ( 2a ) 19 , 6-chloro-9-(prop-2-yn-1-yl)-9 H -purine ( 3a ) 19 , 4-chloro-7-(prop-2-yn-1-yl)-7 H -pyrrolo[2,3- d ]pyrimidine ( 2c ) 20 , 5-fluoro-1-(prop-2-yn-1-yl)-1 H -indole ( 2e ) 21 , 1-(prop-2-yn-1-yl)-1 H -indole ( 2f ) 22 , 1-(prop-2-yn-1-yl)-1 H -benzo[ d ]imidazole ( 2g ) 21 , 1-{[1-(4-fluorophenyl)-1 H -1,2,3-triazol-4-yl]met-hyl}-1 H -benzo[ d ]imidazole ( 12a ) 21 , 1-{[1-(4-chlorophenyl)-1 H -1,2, 3-triazol-4-yl]methyl}-1 H -benzo[ d ]imidazole ( 12b ) 21 , 1-{[1–(4-(trifluoromethyl)phenyl)-1 H -1,2,3-triazol-4-yl]methyl}-1 H -benzo[ d ]imidazole ( 12c) 21 , 1-{[1–(2-fluorophenyl)-1 H -1,2,3-triazol-4-yl]methyl}-1 H -benzo[ d ]imidazole ( 12d ) 21 and 4-{4-[((1 H -benzo[ d ]imidazol-1-yl)methyl)-1 H -1,2,3-triazol-1-yl]methyl}-7-hydroxy-4a,8a-dihydro-2 H -chromen-2-on ( 12e ) 21 and 4-(azidomethyl)-7-hydroxy-2 H -chromen-2-one 23 were prepared according to known procedures.…”

Section: Methodsmentioning

confidence: 99%

Small molecule purine and pseudopurine derivatives: synthesis, cytostatic evaluations and investigation of growth inhibitory effect in non-small cell lung cancer A549

Bistrović

Grbčić

Harej

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

Novel halogenated purines and pseudopurines with diverse aryl-substituted 1,2,3-triazoles were prepared. While p-(trifluoromethyl)-substituted 1,2,3-triazole in N-9 alkylated purine and 3-deazapurine was critical for strong albeit unselective activity on pancreatic adenocarcinoma cells CFPAC-1,1-(p-fluorophenyl)-1,2,3-triazole derivative of 7-deazapurine showed selective cytostatic effect on metastatic colon cancer cells SW620. Importantly, 1-(p-chlorophenyl)-1,2,3-triazole-tagged benzimidazole displayed the most pronounced and highly selective inhibitory effect in nM range on non-small cell lung cancer A549. This compound revealed to target molecular processes at the extracellular side and inside the plasma membrane regulated by GPLD1 and growth factor receptors PDGFR and IGF-1R leading to the inhibition of cell proliferation and induction of apoptosis mediated by p38 MAP kinase and NF-κB, respectively. Further optimisation of this compound as to reduce its toxicity in normal cells may lead to the development of novel agent effective against lung cancer.

show abstract

“…Propargylation reaction (NaH then propargyl bromide in DMF) provides the desired 1-(prop-2-yn-1-yl)-1H-indole-2-carbonitrile 4a in a yield of 75% [10,44]. An efficient method for palladium-catalyzed homocoupling reaction of terminal alkyne in the synthesis of 1H-indole-2-carbonitrile derivatives was carried out (Scheme 2).…”

Section: Synthesis Of 1-(3-phenylprop-2-yn-1-yl)-1h-indole-2-carbonitrile Derivativesmentioning

confidence: 99%

Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

et al. 2021

View full text Add to dashboard Cite

An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

show abstract

[1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole

Cited by 21 publications

References 31 publications

Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids

Some reactions of 2-(4-substitutedphenyl)-2-(N-methyl-N-4-substitutedbenzamido) acetic acids

Small molecule purine and pseudopurine derivatives: synthesis, cytostatic evaluations and investigation of growth inhibitory effect in non-small cell lung cancer A549

Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

Contact Info

Product

Resources

About