Reaction of chromone-3-carboxaldehydes with TOSMIC: synthesis of 4-(2-hydroxybenzoyl)pyrroles

Terzidis, Michael A.; Tsoleridis, Constantinos A.; Stephanidou‐Stephanatou, Julia

doi:10.1016/j.tet.2007.05.100

Cited by 33 publications

(11 citation statements)

References 33 publications

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“…TosMIC has most commonly been used in heterocyclic ring construction, 24 in particular, of oxazole and pyrrole moieties, but comparatively rarely in multicomponent reactions. 25 Since the reaction between imines and TosMIC in basic media constitutes a trusted method for the synthesis of 1,5-disubstituted imidazoles 26 and in continuation to our previous work 27 we speculated that formation of quinoxalines would be possible, through a multicomponent reaction, by using o-phenylenediamines with equimolar amounts of an aldehyde and TosMIC.…”

mentioning

confidence: 84%

Heterocyclizations via TosMIC-Based Multicomponent Reactions: A New Approach to One-Pot Facile Synthesis of Substituted Quinoxaline Derivatives

Neochoritis¹,

Stephanidou‐Stephanatou²,

Tsoleridis³

2009

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A novel multicomponent reaction involving o-phenylenediamines, aldehydes and p-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of a base leading to the formation of quinoxalines in very good yields is described.Quinoxalines are widely used as intermediates in medicinal chemistry, 1,2 since they exhibit a wide range of biological activities, such as antiviral, antibacterial, antiinflammatory and kinase inhibitor properties. 3-10 The echinomycin 11 and the triostins 12 are well-known antibiotic families of quinoxaline derivatives. Furthermore, they have found applications as dyes, 13a efficient electroluminescent materials, 13b organic semiconductors, 13c dehydroannulenes, 13d cavidands 13e and chemically controllable switches. 13f Thus, a number of methods have been developed for the synthesis of substituted quinoxalines involving condensation of 1,2-phenylenediamines with adiketones, also under microwave irradiation, 14 1,4-addition of 1,2-diamines to diazenylbutenes, 15 oxidation trapping of a-hydroxyketones with 1,2-diamines, 16 oxidative cyclization of phenacyl bromides 17 or vicinal diols with ophenylenediamines, 18 oxidative coupling of epoxides 19 or ketones 20 with 1,2-diamines. Very recently, quinoxalines were also synthesized in 33-55% yield, through a twostep reaction sequence, the first step involving a multicomponent reaction between o-phenylenediamines, aldehydes and isonitriles in hydrochloric methanolic solution, whereas in the second step a DDQ oxidation of the isolated dihydroquinoxalines was involved. 21 Sequential transformations and one-pot multicomponent reactions (MCRs) offer significant advantages over conventional linear step syntheses, by reducing time and saving money, energy and raw material thus resulting in both economic and environmental benefits. 22 Moreover, multicomponent synthesis has been established as a valuable tool to the pharmaceutical industry for construction of low molecular weight compound libraries through combinatorial strategies and parallel synthesis. 23 Although p-toluenesulfonylmethyl isocyanide (TosMIC) is a versatile, widely applicable reagent that constitutes a densely functionalized building block bearing an active methylene group apart from its inherent advantage of possessing also an isonitrile functionality, which can serve as a handle for further manipulation, the possibility of its use in multicomponent reactions has not been greatly appreciated. TosMIC has most commonly been used in heterocyclic ring construction, 24 in particular, of oxazole and pyrrole moieties, but comparatively rarely in multicomponent reactions. 25 Since the reaction between imines and TosMIC in basic media constitutes a trusted method for the synthesis of 1,5-disubstituted imidazoles 26 and in continuation to our previous work 27 we speculated that formation of quinoxalines would be possible, through a multicomponent reaction, by using o-phenylenediamines with equimolar amounts of an aldehyde and TosMIC.Initially, a three-component reaction was performed between o-phen...

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confidence: 84%

Heterocyclizations via TosMIC-Based Multicomponent Reactions: A New Approach to One-Pot Facile Synthesis of Substituted Quinoxaline Derivatives
Neochoritis¹,
Stephanidou‐Stephanatou²,
Tsoleridis³
2009
Synlett
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“…The pyrrole 244 is also obtained but in lower yield (~25%) when the above reaction is performed with K 2 CO 3 in MeOH under reflux; use of a strong base like NaOH forms only a small amount of E-Chr-CH=N-CO-Tos along with a polymeric material. 179 Tos CH 2 N C A cascade reaction sequence of [4+2] annulation of the zwitterion 262, generated by addition of tri-n-butylphosphine to the allene 261, with 3-formylchromone followed by deformylation affords in excellent yield and with good diastereoselectivity (~8:1) the tetrahydroxanthone 263 that can be dehydrogenated by DDQ under microwave heating in 1,2-dichlorobenzene to the xanthone 264. 189a This organocatalyzed hetero-Diels-Alder type reaction proceeds well in PhH and PhMe but not in more polar solvents like DCM or THF, and tributylphosphine drives the reaction faster.…”

Section: Scheme 23mentioning
confidence: 99%

Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde
Ghosh¹,
Chakraborty²
2015
Arkivoc
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“…When 3-formylchromones 1a-c,g were allowed to react with equimolar amounts of tosylmethyl isocyanide (TOSMIC) in THF in the presence of mild base as 1,8-diazabicyclo [5,4,0] undec7-ene (DBU) at room temperature, the 2-tosyl-5-(2-hydroxybenzoyl)pyrroles 79 were isolated in good yields (Scheme 38) [65].…”

Section: Scheme 37mentioning
confidence: 99%

“…Interaction of 3-formylchromones 1a-c,g with ethyl glycinate in boiling toluene in the presence of p-toluenesulfonic acid gave a mixture of ethyl 4-(2-hydroxybenzoyl)-6-(4-oxochromen-3-yl)-pyridine-2-carboxylates 169 and ethyl 4-(2-hydroxybenzoyl)pyrrole-2-carboxylates 170 (Scheme 83) [62,65,76,121].…”

Section: Scheme 84mentioning
confidence: 99%

3-Formylchromones as diverse building blocks in heterocycles synthesis
Ali
¹
,
Ibrahim
²
,
El‐Gohary
³

et al. 2013
Eur. J. Chem.
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Reaction of chromone-3-carboxaldehydes with TOSMIC: synthesis of 4-(2-hydroxybenzoyl)pyrroles

Cited by 33 publications

References 33 publications

Heterocyclizations via TosMIC-Based Multicomponent Reactions: A New Approach to One-Pot Facile Synthesis of Substituted Quinoxaline Derivatives

Heterocyclizations via TosMIC-Based Multicomponent Reactions: A New Approach to One-Pot Facile Synthesis of Substituted Quinoxaline Derivatives

Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde

3-Formylchromones as diverse building blocks in heterocycles synthesis

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