Successive Michael reactions on chromone derivatives with dimethyl 1,3-acetonedicarboxylate: one-pot synthesis of functionalized benzophenones, benzo[c]chromones and hydroxybenzoylfuroates

Terzidis, Michael A.; Tsoleridis, Constantinos A.; Stephanidou‐Stephanatou, Julia; Terzis, A.; Raptopoulou, Catherine P.; Psycharis, Vassilis

doi:10.1016/j.tet.2008.10.023

Cited by 30 publications

(18 citation statements)

References 52 publications

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“…In addition, we carried out reactions at reflux in 1,4‐dioxane and in the presence of base (1.3 equiv. ), namely 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) , . The best yield of tetracyclic fused chromone[2,3‐ b ]pyridine derivative 5a (up to 71 %) was obtained by reaction of 3‐methoxalylchromone 1a with 1.1 equiv.…”

Section: Resultsmentioning

confidence: 99%

Reactions of 3‐Acylchromones with Heterocyclic Ketene Aminals: One‐Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives

et al. 2017

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Domino reactions of 3‐acylchromones, namely 3‐methoxalyl‐, 3‐aroyl‐ and 3‐cinnamoylchromones, with heterocyclic ketene aminals (HKAs) proceed by attack of the nucleophile on the C‐2 atom of the chromone moiety, pyrone ring‐opening and subsequent formal [3+3] cyclocondensation with formation of functionalized tetracyclic fused chromeno[2,3‐b]pyridines or 2H,3H‐imidazo[1,2‐a]pyridines. The product distribution depends on the type of acyl group located at the 3‐position of the chromone and on the size of the heterocyclic moiety of the HKAs. The products show considerable activity as selective phosphatase inhibitors.

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Section: Resultsmentioning

confidence: 99%

Reactions of 3‐Acylchromones with Heterocyclic Ketene Aminals: One‐Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives

et al. 2017

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“…In a previous report by Iaroshenko et al., the reactions of 3‐substituted chromones, such as 3‐methoxalyl‐, 3‐polyfluoroacyl‐, and 3‐aroylchromones ( 175 ), with 1,3‐diphenylacetone ( 176 ; Scheme ) or dimethyl 1,3‐acetonedicarboxylate ( 180 ; Scheme ) provided functionalized 2‐hydroxybenzophenones 177 – 179 , 181 , and 182 , benzo[ c ]coumarins 183 , and 6 H ‐benzo[ c ]chromenes 184 depending on the substituent at the 3‐position . In an earlier work, Stephanidou‐Stephanatou and co‐workers similarly demonstrated the synthesis of 2‐hydroxybenzophenones 181 from chromones 175 and dimethyl acetonedicarboxylate 180 by using DBU in THF at room temperature . This transformation proceeded through a Michael addition at the C2 atom of the chromone system, with pyrone ring‐opening and subsequent formal [3+3] cyclocondensation.…”

Section: Dbu‐mediated Benzannulation Reactionsmentioning

confidence: 99%

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

et al. 2018

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Benzene and itsderivativesare the most abundant substructures of several interesting classes of compound, such as bioactive molecules. Owing to their importance, the development of methods for their constructionh as attracted considerable attention.H owever,t he regioselectives ynthesis of polysubstituted aromatic and heteroaromatic compounds by using aromatic substitution is challenging, because it provides derivatives with restricted substitution patterns. Therefore, the benzannulation reaction-the assembly of benzene derivatives from acyclicp recursors-constitutes as uperior and highly versatile approach to polysubstituted aromatic and heteroaromatic compounds,a nd variouse fficient benzannulation reactions have been reported.R epresentative examples include Cs 2 CO 3 , t-BuOK,a nd DBU-catalyzed reactions for the construction of valuableb enzene derivatives. The central objective of this Focus Review is to highlight base-mediated benzannulation reactions under transitionmetal-free conditions for the construction of aromatic and heteroaromatic compounds.[a] Dr.Recently,P an and co-workers investigated the K 2 CO 3 -catalyzed cascade benzannulation reaction of b-keto sulfones 1 with acetylene ketones 2 by using 30 %m ol K 2 CO 3 without other additives,w hich afforded new sulfonylbenzene derivatives 3 in good yields through ab enzannulation reaction (Scheme 1a). [18] Av ariety of electron-donating ande lectron-withdrawing groups were well-tolerated under the optimized reaction conditions. The proposed reactionpathway proceeded through se-quentialM ichael addition, intramolecular cyclization, hydrogen abstraction, and dehydration reactions (Scheme 1b).Scheme55. Synthesis of unsymmetrical biaryls from the annulation/aromatizationr eactionsof1 ,4-pentanedienes with nitroalkanes.Scheme56. DBU-promoted [5+ +1] annulation reaction of a-alkenoyl ketene-S,S-acetalswith nitroalkanes.

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“…When chromones (29) were reacted with dimethyl acetonedicarboxylate (31) in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), 7-hydroxy-6-oxo-6H-benzo[c]chromone-8-carboxylates (30) were furnished as depicted in Scheme 3. 22 This reaction proceeded only for unsubstituted chromones at C-2 and C-3. Methyl groups at C-2 and 3-bromochromone led to the formation of furan derivatives.…”

Section: Cycloaddition Of Dicarbonyl Compounds To Chromonesmentioning

confidence: 99%

Synthetic protocols on 6$H$-benzo[$c$]chromen-6-ones: a review

Mazimba¹

2016

Turk J Chem

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6 H -Benzo[ c ]chromen-6-ones serve as core structures of secondary metabolites and are of considerable pharmacological importance. Natural sources produce limited quantities, hence the need for synthetic procedures for 6 H -benzo[ c ]chromen-6-ones, which are herein reviewed. The literature describes protocols such as the Suzuki coupling reactions for the synthesis of biaryl, which then undergoes lactonization, reactions of 3-formylcoumarin (chromenones) with 1,3-bis(silylenol ethers), radical mediated cyclization of arylbenzoates, metal or base catalyzed cyclization of phenyl-2-halobenzoates and 2-halobenzyloxyphenols, and benzoic acid coupling with benzoquinone using electrophilic metalbased catalyst. The efficient and simple procedures are those involving the reactions of Michael acceptor (chromenones and chalcones) with 1,3-and 1,5-dicarbonyl compounds.

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Successive Michael reactions on chromone derivatives with dimethyl 1,3-acetonedicarboxylate: one-pot synthesis of functionalized benzophenones, benzo[c]chromones and hydroxybenzoylfuroates

Cited by 30 publications

References 52 publications

Reactions of 3‐Acylchromones with Heterocyclic Ketene Aminals: One‐Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives

Reactions of 3‐Acylchromones with Heterocyclic Ketene Aminals: One‐Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

Synthetic protocols on 6$H$-benzo[$c$]chromen-6-ones: a review

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