The synthesis of a coumarin analogue of retinal

Ivanova, Diana; Eremin, S. V.; Швец, В. И.

doi:10.1016/0040-4020(96)00495-4

Cited by 12 publications

(4 citation statements)

References 16 publications

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“…A number of fluorescent 3-arylcoumarins have been synthesised by the photo-coupling of 3-bromocoumarin with aromatic and heteroaromatic compounds [231]. The synthesis of a coumarin, analogue of retinal, that was used for study of the bacteriorhodopsin chromophore binding site, was done via a Wittig olefination of a 3-chloromethylcoumarin (Scheme15) [232].…”

Section: From Arylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

883

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: From Arylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

883

458

View full text Add to dashboard Cite

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“…Numerous approaches to the synthesis of 6 H -dibenzo[ b , d ]pyran-6-ones have been reported. These can be broadly classified according to the bonds formed during the key step(s) as follows: approaches that involve (1) biaryl bond formation followed by lactonization, − (2) construction of an ester or ether followed by intramolecular biaryl bond formation, − (3) a cyclization to form the C ring (or B and C rings), with or without a subsequent aromatization, ,− (4) rearrangement of spirocyclic compounds, − (5) biomemitic syntheses of alternarial derivatives, − and (6) miscellaneous methods. , In category 3, enediyne cycloaromatization, − ruthenium-catalyzed [2+2+2] cycloaromatization, 6π electrocyclic ring closure, condensations involving chromones and coumarins − bearing electron-withdrawing groups, and the Diels–Alder reaction − have been exploited. Of these methods, the Diels–Alder reaction arguably offers the greatest potential for diversity-oriented synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 6H-Dibenzo[b,d]pyran-6-ones Using the Inverse Electron Demand Diels–Alder Reaction

et al. 2011

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A set of coumarin-fused electron-deficient 1,3-dienes was synthesized, which differ in the nature of the electron-withdrawing group (EWG) at the terminus of the diene unit and (when EWG = CO(2)Me) the nature and position of substituents. These dienes reacted with the enamine derived from cyclopentanone and pyrrolidine to afford the corresponding cyclopenteno-fused 6H-dibenzo[b,d]pyran-6-ones, most likely via a domino inverse electron demand Diels-Alder (IEDDA)/elimination/transfer hydrogenation sequence. The parent diene (EWG = CO(2)Me, no substituents) was reacted with a range of electron-rich dienophiles (mostly enamines) to afford the corresponding 6H-dibenzo[b,d]pyran-6-ones or their nondehydrogenated precursors, which were aromatized upon treatment with a suitable oxidant. The enamines could either be synthesized prior to the reaction or generated in situ. The syntheses of 30 dibenzopyranones are reported.

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“…On the basis of the previous reports, , a possible phosphine-mediated cascade process is proposed in Scheme . Initially, a conjugate addition of PPh 3 to acrylamide 1 followed by an intramolecular nucleophilic attack to the aldehyde moiety of 1 (MBH-type reaction) occurred to generate the ylide intermediate Int-I .…”

Section: Resultsmentioning

confidence: 99%

Phosphine-Mediated Morita–Baylis–Hillman-Type/Wittig Cascade: Access to E-Configured 3-Styryl- and 3-(Benzopyrrole/furan-2-yl) Quinolinones

et al. 2022

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A phosphine-mediated, well-designed Morita–Baylis–Hillman-type/Wittig cascade for the rapid assembly of a quinolinone framework from benzaldehyde derivatives is developed for the first time. By rationally combining I2/NIS-mediated cyclization, biologically relevant 3-(benzopyrrole/furan-2-yl) quinolinones were facilely synthesized in a one-pot process by starting from 3-styryl-quinolinones bearing an o-hydroxy/amino group, significantly expanding the chemical space of this privileged skeleton. Further utility of this protocol is illustrated by successfully performing this transformation in a catalytic manner through in situ reduction of phosphine oxide by phenylsilane.

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The synthesis of a coumarin analogue of retinal

Cited by 12 publications

References 16 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Synthesis of 6H-Dibenzo[b,d]pyran-6-ones Using the Inverse Electron Demand Diels–Alder Reaction

Phosphine-Mediated Morita–Baylis–Hillman-Type/Wittig Cascade: Access to E-Configured 3-Styryl- and 3-(Benzopyrrole/furan-2-yl) Quinolinones

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