Synthesis and properties of 3-nitro-2<i>H</i>-chromenes

Korotaev, Vladislav Yu.; Sosnovskikh, Vyacheslav Ya.; Barkov, Alexey Yu.

doi:10.1070/rc2013v082n12abeh004370

Cited by 49 publications

(14 citation statements)

References 91 publications

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“…To prove the plausibility of the one-pot three-component reaction, we commenced our trials with the synthesis and isolation of 3-nitro-2 H -chromene ( 3 ) as reported in the literature [ 15 ], followed by the 1,3-dipolar cycloaddition of the nitroalkene moiety with organic azides. We based the 1,3-dipolar cycloaddition reaction on the synthesis of NH -triazoles by Guan et al using p -toluenesulfonic acid as the catalyst in DMF [ 19 ], but with benzyl azide ( 4a ) instead of sodium azide ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Hence, the search for new methodologies towards the rapid assembly of chromene analogs is of utmost importance for many researchers. In this regard, 3-nitrochromenes are easily available building blocks for chromene and chromane derivatives and are highly reactive due to the presence of the nitroalkene moiety, which enables them to undergo a high variety of reactions and functionalizations [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

“…Hence, in our continued exploration towards novel multicomponent reactions for the assembly of triazole-fused (hetero)cycles [ 24 , 33 – 42 ], we opted to develop a new one-pot two-step three-component reaction starting from salicylaldehydes, nitroalkenes and organic azides, without isolation of the intermediate 3-nitrochromenes, in a regioselective manner and without the use of metals. Salicylaldehydes with a high melting point or low solubility proved difficult to convert to the intermediate 3-nitrochromene derivatives [ 15 ]. In this regard, applying mechanochemistry has been proven previously to be a viable alternative [ 43 ].…”

Section: Introductionmentioning

confidence: 99%

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Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

Vroemans

Verhaegen

Dieu

et al. 2018

Beilstein J. Org. Chem.

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A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a 1,3-dipolar cycloaddition of the intermediate 3-nitro-2H-chromenes with organic azides in a one-pot two-step sequence. The triazolochromenes were formed with complete regioselectivity and new biologically relevant structures were synthesized via extension of the developed procedure and via postfunctionalization. The mechanochemical synthesis was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

Vroemans

Verhaegen

Dieu

et al. 2018

Beilstein J. Org. Chem.

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“…This increase in research is mainly due to the fact that new types of simple and ecological synthetic pathways have been described, among which are those carried out in the absence of solvents, as the processes developed in this work, and which are part of what is known as "Green Chemistry". Another reason why 3nitro-2H-chromenes are being studied is that these compounds are widely distributed in the plant kingdom and their activity as effective pesticides and pharmacophores has been recognised [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antiproliferative activity of new 2-glyco-3-nitro-2H-chromenes

Luque-Agudo

Albarrán-Velo

Light

et al. 2019

Bioorganic Chemistry

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3-nitro-2H-chromenes and derivatives are compounds with diverse biological activity, among them, new 2-glyco-3-nitro-2H-chromenes have been prepared by one-pot oxa-Michael-Henrydehydration reactions between carbohydrate-derived nitroalkenes and several salicylaldehydes, using a minimal amount of solvent and DBU as catalyst. The antiproliferative activity of these new compounds has been evaluated against a panel of six human solid tumor cell lines, and compared to pharmacological reference compounds, finding that their activities are in the low micromolar range and that some of them are more effective than the standards.

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“…[1][2][3] Due to their versatile transformations in synthetic chemistry, a simple and efficient preparation of these valuable bulding blocks has drawn much attention from synthetic chemists. [4][5][6] The tandem oxa-MichaelHenry reaction of salicylaldehyde with β-nitrostyrenes is considered to be the most straightforward for preparation of 2-aryl-3-nitro-2H-chromenes. Several reports describe construction of 2-aryl-3-nitro-2H-chromenes in good yields using 1,4-diazabicyclo[2.2.2]octane (DABCO), 7,8 L-pipecolinic acid 9 or C 2 -symmetric pyrrolidine-triazoles 10 as catalysts.…”

Section: Introductionmentioning

confidence: 99%

Facile access to 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes

Wang¹,

Zhang²,

Liu³

2014

Arkivoc

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Using salicylaldehydes and β-nitrostyrenes as starting materials, 2-aryl-3-nitro-2H-chromenes were prepared in good yields (up to 83%) through the combination of 30 mol% of pyrrolidinebenzoic acid catalyzed tandem oxa-Michael-Henry reactions in refluxing ethanol. Additionally, the Michael reactions of 2-aryl-3-nitro-2H-chromenes with acetone were also performed by the same catalytic combination in brine to give 2,3,4-trisubstituted chromanes up to 86% yield with excellent stereoselectivities. The structures of 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes are confirmed by X-ray single crystal diffraction analysis. The reductive amination of a suitable 2,3,4-trisubstituted chromane with Zn/HOAc affords a fused tricyclic amine in 92% yield.

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Synthesis and properties of 3-nitro-2H-chromenes

Cited by 49 publications

References 91 publications

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

Synthesis and antiproliferative activity of new 2-glyco-3-nitro-2H-chromenes

Facile access to 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes

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