Literature DB >> 19921455

Electrochemically induced multicomponent assembling of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile: a convenient and efficient way to functionalized spirocyclic [indole-3,4'-pyrano[3,2-c]quinoline] scaffold.

Michail N Elinson1, Valentina M Merkulova, Alexey I Ilovaisky, Dmitry V Demchuk, Pavel A Belyakov, Gennady I Nikishin.   

Abstract

Electrochemically induced catalytic multicomponent transformation of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized indole-3,4'-pyrano[3,2-c]quinoline] scaffold in 75-91% substance yields and 500-600% current yield. The developed efficient electrocatalytic approach to medicinally relevant [indole-3,4'-pyrano[3,2-c]quinoline] scaffold is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel example of facile environmentally benign synthetic concept for electrocatalytic multicomponent reactions.

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Year:  2009        PMID: 19921455     DOI: 10.1007/s11030-009-9207-z

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  9 in total

1.  Electrocatalytic multicomponent assembling of isatins, 3-methyl-2-pyrazolin-5-ones and malononitrile: facile and convenient way to functionalized spirocyclic [indole-3,4'-pyrano[2,3-c]pyrazole] system.

Authors:  Michail N Elinson; Alexander S Dorofeev; Fedor M Miloserdov; Gennady I Nikishin
Journal:  Mol Divers       Date:  2008-12-02       Impact factor: 2.943

2.  Screening of cytotoxic activities of Strychnos alkaloids (methods and results).

Authors:  J Leclercq; M C De Pauw-Gillet; R Bassleer; L Angenot
Journal:  J Ethnopharmacol       Date:  1986-03       Impact factor: 4.360

Review 3.  Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

Authors:  Robert M Williams; Rhona J Cox
Journal:  Acc Chem Res       Date:  2003-02       Impact factor: 22.384

4.  Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists.

Authors:  B E Evans; K E Rittle; M G Bock; R M DiPardo; R M Freidinger; W L Whitter; G F Lundell; D F Veber; P S Anderson; R S Chang
Journal:  J Med Chem       Date:  1988-12       Impact factor: 7.446

Review 5.  2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes.

Authors:  Jacques Poupaert; Pascal Carato; Evelina Colacino; Saïd Yous
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

6.  New phenylpropenoids, bis(1-phenylethyl)phenols, bisquinolinone alkaloid, and anti-inflammatory constituents from Zanthoxylum integrifoliolum.

Authors:  Jih-Jung Chen; Po-Hou Chen; Chang-Hui Liao; Shi-Yu Huang; Ih-Sheng Chen
Journal:  J Nat Prod       Date:  2007-09-07       Impact factor: 4.050

7.  Structural simplification of bioactive natural products with multicomponent synthesis. 2. antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones.

Authors:  Igor V Magedov; Madhuri Manpadi; Marcia A Ogasawara; Adriana S Dhawan; Snezna Rogelj; Severine Van Slambrouck; Wim F A Steelant; Nikolai M Evdokimov; Pavel Y Uglinskii; Eerik M Elias; Erica J Knee; Paul Tongwa; Mikhail Yu Antipin; Alexander Kornienko
Journal:  J Med Chem       Date:  2008-03-25       Impact factor: 7.446

8.  Chemical and bioactive constituents from Zanthoxylum simulans.

Authors:  I S Chen; S J Wu; I L Tsai
Journal:  J Nat Prod       Date:  1994-09       Impact factor: 4.050

Review 9.  Quinoline, quinazoline and acridone alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2007-12-17       Impact factor: 13.423

  9 in total

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