Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N,N-Dimethylbenzylamine

Kiyani, Hamzeh; Jalali, Mohammadreza

doi:10.3987/com-15-13360

Cited by 20 publications

(5 citation statements)

References 49 publications

(36 reference statements)

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“…Since the compound containing 4 H -pyrans has outstanding biological properties and pharmaceutical applications, several synthetic methods have now been published in the literature − using several catalysts, such as carbon-based solid acids, montmorillonite perchloric acid (MPA), MgO NPs, Zn( l -proline) 2 , cyclodextrin, THEIC-SBA-15, urea, TMDPS, Fe 3 O 4 @D-NH-(CH 2 ) 4 -SO 3 H, TiO 2 –CNT nanocomposite, [BMIm]BF 4 , Na 2 CO 3 , Mo catalyst, nano-TiO 2 /H 14 [NaP 5 W 30 O 110 ], V-complex, [HMIM]C(CN) 3 , trifluoroethylene (TFE), supported-KF, urea, nanozeolite, Fe 3 O 4 @SiO 2 -imid–PMA, etc. Undoubtedly, these reported methods have their advantages.…”

Section: Introductionmentioning

confidence: 99%

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Patra,

Nandi,

Maurya

et al. 2024

ACS Omega

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In this report, four new Ni(II)−unsymmetrical salen complexes, [NiL 1−4 ], were prepared by refluxing Ni(Ac) 2 •4H 2 O with unsymmetrical salen ligands, H 2 L 1−4 . All of the synthesized ligands and complexes were characterized by various physicochemical methods. Also, the solid-state structures of [NiL 1 ], [NiL 2 ], and [NiL 4 ] were defined through single-crystal X-ray diffraction methods. The catalytic potential of [NiL 1−4 ] was investigated by economic and environmentally friendly one-pot-three-component reactions (using reagent: 1,3-dicarbonyls, malononitrile, benzaldehyde, or its derivatives) for the synthesis of biologically active 2amino-3-cyano-4H-pyran derivatives (total 16 derivatives). After optimization of the reaction conditions, this new synthetic protocol by taking Ni(II)−unsymmetrical salen complexes as catalysts shows excellent conversion with a maximum yield of up to 98% of the effective catalytic products within 1 h of reaction time. In addition, it was observed that the aromatic aldehyde containing an electron-withdrawing group as a ring substituent shows better conversion (up to 98%), and the electron-donating group substituent shows similar or less conversion compared to benzaldehyde under the optimized reaction conditions. From the comparison of results between all these Ni complexes, it was found that the efficiency of the catalytic performance follows the order [NiL 1 ] > [NiL 3 ] > [NiL 2 ] > [NiL 4 ]. A possible reaction pathway was predicted and established through UV−vis spectroscopy. Intermediate II proposed in the reaction pathway was also trapped and characterized through 1 H and 13 C NMR.

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Section: Introductionmentioning

confidence: 99%

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Patra,

Nandi,

Maurya

et al. 2024

ACS Omega

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“…Furthermore, numerous effective synthetic methods have been recorded for generating 2-amino-4H-pyran-3-carbonitrile intermediates. [53][54][55][56][57][58][59][60][61][62] Therefore, as part of our ongoing research focused on the discovery of novel bioactive compounds, [63][64][65][66][67] in this study, we focused on the synthesis and biological evaluation of novel pyrano[2,3-d ]pyrimidine compounds 8a-k. The newly synthesized molecules were evaluated for their AChE inhibitory activity, along with an evaluation of their cytotoxicity, to investigate their potential for use in treating AD.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Acetylcholinesterase Inhibitory and Cytotoxic Activities of Pyrano[2,3-d]pyrimidines

Thanh,

Giang,

et al. 2023

Natural Product Communications

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Objective: The study was conducted to evaluate the in vitro acetylcholinesterase (AchE) inhibition activity of novel pyrano[2,3- d]pyrimidine derivatives. Methods: A series of new pyrano[2,3- d]pyrimidine derivatives were synthesized in moderate to good yields (63%-81%) by using microwave-prompted “one-pot” two-step multicomponent reactions of cyclohexane-1,3-dione, malononitrile, aldehydes, and acetic anhydride. Noticeably, Diazabicyclo[2.2.2]octane was successfully employed as a basic catalyst for the formation of 2-amino-4H-pyran-3-carbonitrile intermediates. These products were identified using spectral data, and assessed in terms of their AChE inhibition activity and cytotoxicity against three types of human cancer cell lines including epidermoid carcinoma (KB), hepatoma carcinoma (HepG2), and non-small lung cancer (A549) cell lines. Results: Most of the products depicted moderate to good AChE inhibitory activity, among them, one product with methoxy moiety at meta-position on phenyl group showed the best AchE inhibition activity with IC50 values of 2.20 ± 0.17 µg/mL. Moreover, products exhibited no cytotoxicity against cancer cell lines. Conclusion: This study highlighted that pyrano[2,3- d]pyrimidine derivatives as promising candidates for further investigations directed to the discovery of new AChE inhibitors which could be used in Alzheimer's disease therapy.

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“…19 Several methods have been reported for synthesizing tetrahydrobenzo[b]pyrans via a three-component condensation process with aryl aldehydes, dimedone, and malononitrile, using a variety of catalysts and under diverse reaction conditions. [20][21][22][23][24][25][26][27][28][29][30][31][32][33] Although some of these protocols are satisfactory, many suffer from drawbacks such as extended reaction times, complex work-up processes, and the use of expensive and hazardous catalysts. As a result, researchers are increasingly motivated to design and develop synthetic processes that are more environmentally benign and sustainable in light of the growing demand for a cleaner future.…”

Section: Introductionmentioning

confidence: 99%

A redox active organodiselenide as an efficacious catalyst for the synthesis of oxygen-containing heterocyclic compounds

Rahman,

Kushwah,

Priyadarsini

2023

New J. Chem.

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Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N,N-Dimethylbenzylamine

Cited by 20 publications

References 49 publications

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Synthesis and Evaluation of Acetylcholinesterase Inhibitory and Cytotoxic Activities of Pyrano[2,3-d]pyrimidines

A redox active organodiselenide as an efficacious catalyst for the synthesis of oxygen-containing heterocyclic compounds

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