Indolizines. 4. Dyes derived from oxoindolizinium ions and active methylene compounds

Weidner, Charles H.; Wadsworth, Donald H.; Bender, Steven L.; Beltman, D. J.

doi:10.1021/jo00276a029

Cited by 57 publications

(19 citation statements)

References 2 publications

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“…Indolizines represent interesting targets in synthetic chemistry due to the fact that they offer manifold applications as e. g. dyes [1], pharmaceuticals [2], and spectral sensitizers [3 -7]. While aromatic indolizines are very scarce in nature, the fully reduced form of these heteroaromatic bicyclic compounds, the so-called indolizidines, are quite common [8].…”

Section: Introductionmentioning

confidence: 99%

One-pot Synthesis of 3-Aryl-substituted 1-Hydroxy-2-acylindolizines

Kloubert

Kretschmer

Görls

et al. 2012

Zeitschrift Für Naturforschung B

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A new method for the formation of C-C bonds in a one-pot synthesis of 1-hydroxy-2-acyl-3-arylindolizines (acyl: 2-pyridylformyl, thienylformyl; aryl: phenyl, pyridyl, thienyl) from the reaction of 1,3-diketones with aldehydes has been evaluated. X-Ray diffraction studies of single crystals have provided structural information about the so-formed indolizines. In the crystalline state, the hydroxyl units form intra-or intermolecular hydrogen bonds to the acyl functionalities. The color of these indolizines depends on the pH value of the solvent.

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Section: Introductionmentioning

confidence: 99%

One-pot Synthesis of 3-Aryl-substituted 1-Hydroxy-2-acylindolizines

Kloubert

Kretschmer

Görls

et al. 2012

Zeitschrift Für Naturforschung B

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“…Some of the marketed drugs such as zolpidem, saripidem, alpidem, zolimidine, olprinone and necopidem contain indolizine scaffold. Indolizine derivatives have been widely employed as molecular probes in the field of material sciences, such as dye sensitized solar cells (DSSC), (Figure 1) organic light‐emitting devices (OLEDs), biomarkers and dyes . Also, they have a long‐wavelength both in absorption and fluorescence with moderately high quantum efficiency in the visible‐light region…”

Section: Introductionmentioning

confidence: 99%

Catalyst free Synthesis of Highly Functionalized Indolizines from In Situ Generated Pyridinium Ylides via One‐Pot Multicomponent Reaction

Ramesh

Devi²,

Velusamy

et al. 2019

ChemistrySelect

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A base-promoted one-pot three-component domino reaction of in situ generated pyridinium ylides with α-oxoketene dithioacetals (AKDTAs) lead to synthesis of indolizine derivatives. In this one-pot transformation, three new bonds and one new ring was efficiently formed in one sequence. The current method provides a simple, convenient route for the synthesis of biologically important indolizine derivatives without using any catalyst in good yield. The synthesized compound 4 g was confirmed by single crystal X-ray analysis.[a] V.

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“…The interest in these compounds is largely owing to their properties. Synthetic indolizines are used as potential central nervous system depressants [1], calcium entry blockers [2], testosterone 5α‐reductase inhibitors [3], cardiovascular agents [4], spectral sensitizers [5], and novel dyes [6]. Pyrrolo[2,1‐ a ]isoquinoline derivatives [7] have attracted considerable interest, because they possess antidepressant [8], muscarinic agonist [9], antiplatelet [10], and anticancer activity [11].…”

Section: Introductionmentioning

confidence: 99%