One-pot Synthesis of 2-Amino-2-chromene and 2-Amino-3-cyano-4H-pyran Derivatives Promoted by Potassium Fluoride

Maleki, Behrooz; Sheikh, Safoora

doi:10.1080/00304948.2015.1066647

Cited by 60 publications

(13 citation statements)

References 39 publications

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“…In continuation of our previous work on the development of new synthetic methods [52][53][54][55][56][57][58][59][60][61][62][63], in this research, an advance in the synthesis of biologically important materials, use of a separable magnetic nano catalyst, NFS-PWA, is reported. This new environmentally benign, heterogeneous, and highly re-usable catalyst had very good catalytic activity in the preparation of tetrahydrobenzo[b]pyrans and pyrano[2,3-c]pyrazoles (Scheme 1).…”

Section: Resultsmentioning

confidence: 95%

Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives

et al. 2015

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A powerful, magnetic, supported, acid catalyst, NiFe 2 O 4 @SiO 2 -H 3 PW 12 O 40 , was prepared by chemical support of Keggin (H 3 PW 12 O 40 ) heteropolyacid (HPA) on silica-coated NiFe 2 O 4 magnetic nanoparticles. XRD, TEM, SEM, VSM, and FTIR confirmed that the keggin HPA is well dispersed on the surface of silica-coated NiFe 2 O 4 magnetic nanoparticles. The magnetically recoverable catalyst could be easily recycled at least six times without significant loss of catalytic activity. After full characterization, its catalytic activity was investigated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives. Graphical Abstract (1) Novel silica-coated magnetic NiFe 2 O 4 nanoparticles-supported H 3 PW 12 O 40 was fabricated and characterized. (2) Recyclability of the catalyst. (3) Avoiding use of corrosive acid catalysts. (4) Green chemistry.

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Section: Resultsmentioning

confidence: 95%

Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives

et al. 2015

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“…Such compounds were applicable in the field of pharmaceutical drugs; thus, they have a wide range of applications within the organic synthesis . Moreover, through the field of industrial chemistry and fabric productions, these compounds have many applications like their uses as cosmetics and pigments this is in addition to their biodegradable agrochemical applications . On the other side, 1,3‐dicarbonyl compounds, cyclohexane‐1,3‐dione, and its derivative 5,5‐dimethyl cyclohexane‐1,3‐dione (dimedone) are well known as reactive starting compounds that are ready for many heterocyclic transformations .…”

Section: Introductionmentioning

confidence: 99%

Uses of Cyclohexan-1,3-dione for the Synthesis of Thiazole, Pyrazole, Thiophene, Isoxazole and Pyran Derivatives with Antitumor Activities

Mohareb

Abdo

Al-darkazali

2020

LDDD

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Cyclohexan‐1,3‐dione (1) was used as the key starting material, which reacted with salicylaldehyde (2) and either malononitrile (3a) or ethyl cyanoacetate (3b) in ethanol containing a catalytic amount of triethylamine to give the 3,4,7,12b‐tetrahydrochromeno[3,4‐c]chromen‐1‐one derivatives 5a,b. The latter compounds underwent Gewald's thiophene synthesis through the reaction with either malononitrile or ethyl cyanoacetate to give compounds 6a‐d, respectively. On the other hand, compound 5a was used for the synthesis of annulated chromeno[3,4‐c]chromen derivatives through its reaction with different chemical reagents. The synthesized compounds were evaluated against the six cancer cell lines A549, HT‐29, MKN‐45, U87MG, SMMC‐7721, and H460 using the standard MTT assay in vitro, with foretinib as the positive control, many compounds expressed high inhibitions. The most active compounds 5b, 6b, 6d, 7, 9b, 11a, 11b, 13, 17, 18b, 20b, 21b, 21e, and 21f were selected for inhibition of five tyrosine kinases and some selected compounds for Pim‐1 kinase inhibition. The results showed that compounds 6b, 6d, 11a, 13, 17, 20b, and 21e were the most potent compounds with the tyrosine kinases and compounds 6d, 11a, 20b, and 21e were the most potent inhibitors of Pim‐1 kinase.

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“…Furthermore, 4 H‐ pyrans are building blocks for some important natural products . A number of 2‐amino‐4 H‐ pyrans are used as photoactive materials , pigments , and potentially biodegradable agrochemicals . Because they possess unique pharmacological properties, new methodologies for the synthesis of these compounds have emerged.…”

Section: Introductionmentioning

confidence: 99%

Microwave Synthesis of Fused Pyrans by Humic Acid Supported Ionic Liquid Catalyst and Their Antimicrobial, Antioxidant, Toxicity Assessment, and Molecular Docking Studies

Thangaraj

Ranjan

Ramesh

et al. 2019

Journal of Heterocyclic Chem

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A series of fused quinolinyl and quinolonyl pyrans were synthesized via a one‐pot reaction of quinolinyl and quinolonyl carbaldehydes, malononitrile, and a 1,3‐diketone. The reactions were catalyzed by a new humic acid supported 1‐butyl‐3‐methyl imidazolium thiocyanate ionic liquid under microwave irradiation conditions. Antimicrobial, antioxidant, and toxicity studies displayed various biological activities depending on structure of the pyrans.

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One-pot Synthesis of 2-Amino-2-chromene and 2-Amino-3-cyano-4H-pyran Derivatives Promoted by Potassium Fluoride

Cited by 60 publications

References 39 publications

Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives

Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives

Uses of Cyclohexan-1,3-dione for the Synthesis of Thiazole, Pyrazole, Thiophene, Isoxazole and Pyran Derivatives with Antitumor Activities

Microwave Synthesis of Fused Pyrans by Humic Acid Supported Ionic Liquid Catalyst and Their Antimicrobial, Antioxidant, Toxicity Assessment, and Molecular Docking Studies

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