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TetrahedronVolume 69, Issue 10, 11 March 2013, Pages 2309-2318

Efficient synthesis of novel benzo[b][1,8]naphthyridin-4(1H)-ones and pyrido[2,3-b]quinoxalin-4(1H)-ones from alkynones and primary amines(Article)(Open Access)

  • Iaroshenko, V.O.,
  • Zahid, M.,
  • Mkrtchyan, S.,
  • Gevorgyan, A.,
  • Altenburger, K.,
  • Knepper, I.,
  • Villinger, A.,
  • Sosnovskikh, V.Y.,
  • Langer, P.
  • View Correspondence (jump link)
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  • aInstitut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
  • bNational Taras Shevchenko University, 62 Volodymyrska Str., 01033 Kyiv, Ukraine
  • cDepartment of Chemistry, Ural Federal University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
  • dLeibniz-Institut für Katalyse An der Universität Rostock E.V., Albert Einstein Str. 29a, 18059 Rostock, Germany

Abstract

An efficient palladium-catalyzed cyclization of o-chlorohetaryl ynones with aliphatic and aromatic primary amines represents a simple access to a wide range of benzo[b][1,8]naphthyridin-4(1H)-one and pyrido[2,3-b]quinoxalin-4(1H)- one derivatives in good to excellent yields. © 2013 Elsevier Ltd. All rights reserved.

Author keywords

AminesBenzo[b][1,8]naphthyridin-4(1H)-oneso-Chlorohetaryl ynonesPalladium-catalyzed cyclizationPyrido[2,3-b]quinoxalin-4(1H)-ones

Indexed keywords

EMTREE drug terms:1 (2 chlorobenzyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (2 fluorophenyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (2 hydroxyethyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (2 hydroxyethyl) 2 phenylpyrido[2,3 b]quinoxalin 4(1h) one1 (3 chloroquinoxalin 2 yl) 3 phenylprop 2 yn 1 one1 (3 chloroquinoxalin 2 yl)undec 2 yn 1 one1 (3 methoxybenzyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (3 morpholinopropyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (3,4 dimethoxyphenyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (3,5 dimethoxyphenyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (4 ethylphenyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (4 methoxybenzyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 (4 methoxyphenyl) 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 [3 (1h imidazol 1 yl)propyl] 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 [4 (diethylamino)phenyl] 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 benzyl 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 benzyl 2 phenylpyrido[2,3 b]quinoxalin 4(1h) one1 cyclohexyl 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 cyclohexyl 2 phenylpyrido[2,3 b]quinoxalin 4(1h) one1 cyclopropyl 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 heptyl 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one1 phenethyl 2 phenylbenzo[b][1,8]naphthyridin 4(1h) one2 phenyl 1 (2,4 dimethoxyphenyl)benzo[b][1,8]naphthyridin 4(1h) one2 phenyl 1 (3,4,5 trimethoxyphenyl)benzo[b][1,8]naphthyridin 4(1h) one2 phenyl 1 (3,5 dimethylphenyl)benzo[b][1,8]naphthyridin 4(1h) one2 phenylbenzo[b][1,8]naphthyridin 4(1h) onearomatic aminepyridine derivativequinoxaline derivativeunclassified drugunindexed drug
EMTREE medical terms:aminationarticlecarbon nuclear magnetic resonancecolumn chromatographycyclizationdrug structuredrug synthesismass spectrometrypriority journalproton nuclear magnetic resonance

Funding details

Funding sponsor Funding number Acronym
Deutscher Akademischer Austauschdienst
See opportunities by DAAD		DAAD

  • 1

    Financial support by DAAD (scholarships for S.M. and A.G.) is gratefully acknowledged.

  • ISSN: 00404020
  • CODEN: TETRA
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/j.tet.2013.01.008
  • Document Type: Article

  Iaroshenko, V.O.; Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, Germany;
© Copyright 2013 Elsevier B.V., All rights reserved.

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