New conversions of pyridinium salts and syntheses of γ-amino-substituted pyridines

Vompe, A. F.; Monitch, N.V.; Turitsyna, N. F.; Ivanova, Natalia V.

doi:10.1016/0040-4020(58)88063-1

Cited by 8 publications

(2 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Treatment of 7a 7b with ammonium acetate gave 4-amino compound 8a, which was converted to its bromide 9a. 9 Palladium-mediated cross-coupling reaction of 9a and ethoxyvinyltributyltin provided 10a, which was subsequently hydrolyzed to furnish 11a. 10 The corresponding 4-methoxy analogue 11c was prepared in a similar way.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Discovery of Orally Efficacious Tetracyclic Metabotropic Glutamate Receptor 1 (mGluR1) Antagonists for the Treatment of Chronic Pain

Wu¹,

Burnett²,

Domalski³

et al. 2007

J. Med. Chem.

View full text Add to dashboard Cite

Metabotropic glutamate receptor 1 (mGluR1) plays important roles in the neurotransmission and pathogenesis of several neurological disorders, including chronic pain. Antagonists of mGlur1 are suggested to be useful for the treatment of pain. Herein, we report the discovery of a novel series of tetracyclic mGluR1 antagonists, such as 23c and 23e, with oral efficacy of ED50 of 8 and 5.1 mg/kg, respectively, in rat spinal nerve ligation neuropathic pain model.

show abstract

mentioning

confidence: 99%

“…The synthesis of the pyrrolo analogues 11a − c is outlined in Scheme . Treatment of 7a 7b with ammonium acetate gave 4-amino compound 8a , which was converted to its bromide 9a .…”

mentioning

confidence: 99%

Discovery of Orally Efficacious Tetracyclic Metabotropic Glutamate Receptor 1 (mGluR1) Antagonists for the Treatment of Chronic Pain

Wu¹,

Burnett²,

Domalski³

et al. 2007

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

Pyridinols and Pyridones

Meislich

1962

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

Neuere Methoden der präparativen organischen Chemie II. 12. Die Einführung von Substituenten in den Pyridin‐Ring

Thomas

Jerchel

1958

Angewandte Chemie

View full text Add to dashboard Cite

Der Pyri,din-Ring läßt sich nur schwer substituieren, da der aromatisch gebundene Ringstickstoff wie ein Substituent zweiter Ordnung die Reaktionsfähigkeit der Molekel stark herabsetzt. Ein elektrophiler Substituent t r i t t daher nur bei hohen Temperaturen und langen Reaktionszeiten ausschließ-lich in die 3-bzw. 5-Stellung ein. Die Umsetzung mit nucleophilen Partnern ist dagegen wesentlich leichter möglich und führt überwiegend zu einer Substitution der 2-StelIung. Isomerengemische treten auf, wenn man Pyridin mit Radikalen reagieren läßt. Zur Substitution der U-Stellung des PyridinKerns finden vor allem Pyridiniumsalze, 4-Pyridyl-pyridiniumsalze und Pyridin-N-oxyde Verwendung.

show abstract

New conversions of pyridinium salts and syntheses of γ-amino-substituted pyridines

Cited by 8 publications

References 6 publications

Discovery of Orally Efficacious Tetracyclic Metabotropic Glutamate Receptor 1 (mGluR1) Antagonists for the Treatment of Chronic Pain

Discovery of Orally Efficacious Tetracyclic Metabotropic Glutamate Receptor 1 (mGluR1) Antagonists for the Treatment of Chronic Pain

Pyridinols and Pyridones

Neuere Methoden der präparativen organischen Chemie II. 12. Die Einführung von Substituenten in den Pyridin‐Ring

Contact Info

Product

Resources

About