Nuclear magnetic resonance. Part IV. The protonation of indolizines

Fraser, M.; McKenzie, S.; Reid, D. H.

doi:10.1039/j29660000044

Cited by 23 publications

(21 citation statements)

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“…HPLC-MS analysis after only 10 minutes indicated no remaining intermediate 6d; however, a new signal with a mass corresponding to that of the pyrroloisoquinoline 10da was present. It has been shown previously that indolizines form salts with strong acids, 32 hence the TFA was removed with a base rather than by evaporation. After removing the TFA by addition of macroporous polymer-supported carbonate (PS-CO 3 ), crude 10da was purified by column chromatography and crystallised 31 as yellow crystals (47% yield).…”

Section: One-pot Reactionmentioning

confidence: 99%

A New Focused Microwave Approach to the Synthesis of Amino-Substituted Pyrroloisoquinolines and Pyrroloquinolines via a Sequential Multi-Component Coupling Process

Hopkin¹,

Baxendale²,

Ley³

2008

Synthesis

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A multi-component reaction has been developed allowing direct access to pyrroloisoquinolines and pyrroloquinolines with new, electron-rich substitution patterns. The synthesised amino-substituted heterocyclic compounds and intermediates involved in their formation represent novel compounds. Focused microwave irradiation was used extensively to allow simple access to a wide temperature range using low boiling point solvents.

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Section: One-pot Reactionmentioning

confidence: 99%

A New Focused Microwave Approach to the Synthesis of Amino-Substituted Pyrroloisoquinolines and Pyrroloquinolines via a Sequential Multi-Component Coupling Process

Hopkin¹,

Baxendale²,

Ley³

2008

Synthesis

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“…In the 1 H-NMR spectrum, there was a singlet of double intensity of H-3 at 5.8 ppm, while the rest of the signals were shifted downfield. The literature data of the spectra of 1- and 3-CH 2 -indolizyl cations [ 14 , 15 , 16 ] indicate that the position of a singlet of the CH 2 group at δ > 5 ppm is clear proof of protonation at position 3. Since the protonated atom C-3 is excluded from the π-excessive heterocyclic system, its subsequent acylation becomes impossible.…”

Section: Resultsmentioning

confidence: 99%

Reactions of 5-Indolizyl Lithium Compounds with Some Bielectrophiles

et al. 2017

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“…Synthese. -Indolizine sind schwache Basen, die an C(1), jedoch uberwiegend an C(3) protoniert werden [5] [6]. Die Ladungsdichteverteilung in diesem Molekul war schon mehrfach Gegenstand von Berechnungen.…”

Section: D'unclassified

Halochrome Molekeln. 5. Mitteilung. Synthese substituierter 6H‐Chromeno[4,3‐b]indolizine und ihrer Aza‐analogen

Gunzenhauser¹,

Balli²

1985

Helvetica Chimica Acta

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Halochromic Molecules. Synthesis o f Substituted 6H-Chromeno[4,3-b lindolizines and their Aza-analoguesWe have synthesized a series of substituted chromeno [4,3-h]indolizines and their respective aza-analogues. Dyes generated from them contain the electrondonating 2-(2-hydroxy-5-methyIphenyl)indolizin-3-yl moiety. The 90 MHz FT 'H-NMR spectra of starting and final products supported the postulated structures. Fragmentations in the mass spectra also were consistent with the assumed structures.1. Einleitung. -Chromogene vom Typus der substituierten Phthalide werden haufig in chemischen Durchschreibesystemen eingesetzt. Ihre Vorteile sind die hohe Farbstarke der erzeugten Triarylmethanfarbstoffe bei langwelliger Absorption und ihre relativ leichte Zuganglichkeit.Ersetzt man im Triarylcarbeniumion Aryl-durch einen Heteroaryl-Rest, der zudem an geeigneter Stelle eine phenolische OH-Gruppe tragt, so sind diese Molekule nach der Deprotonierung dieses Substituenten zu einem internen Ringschluss befahigt, der zu farblosen bis gelben Chromogenen fiihrt. In fruheren Arbeiten wurden halochrome Verbindungen mit 2-(2-Hydroxyphenyl)-3-indolyl als Heteroarylrest eingehend unter-

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Nuclear magnetic resonance. Part IV. The protonation of indolizines

Cited by 23 publications

References 0 publications

A New Focused Microwave Approach to the Synthesis of Amino-Substituted Pyrroloisoquinolines and Pyrroloquinolines via a Sequential Multi-Component Coupling Process

A New Focused Microwave Approach to the Synthesis of Amino-Substituted Pyrroloisoquinolines and Pyrroloquinolines via a Sequential Multi-Component Coupling Process

Reactions of 5-Indolizyl Lithium Compounds with Some Bielectrophiles

Halochrome Molekeln. 5. Mitteilung. Synthese substituierter 6H‐Chromeno[4,3‐b]indolizine und ihrer Aza‐analogen

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