Literature DB >> 25758539

A one-pot three-component reaction involving 2-aminochromone in aqueous micellar medium: a green synthesis of hexahydrochromeno[2,3-b]quinolinedione.

Jaydip Ghosh1, Pritam Biswas, Michael G B Drew, Chandrakanta Bandyopadhyay.   

Abstract

An efficient and green synthesis of hitherto unreported 11-(chromen-3-yl)-8,8-dimethyl-8,9-dihydro-6H-chromeno[2,3-b]quinoline-10,12(7H,11H)-dione has been accomplished by a three-component reaction involving 2-aminochromone, chromone-3-carbaldehyde, and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) in 0.5 M aqueous SDS solution. The mechanism of the reaction has been studied by isolating the reaction intermediate. This methodology features eco-friendly reaction conditions, a simple working procedure, high atom-economy and high efficiency in product formation.

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Year:  2015        PMID： 25758539     DOI： 10.1007/s11030-015-9573-7

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


  23 in total

1.  Synthesis of new cis-fused tetrahydrochromeno[4,3-b]quinolines and their antiproliferative activity studies against MDA-MB-231 and MCF-7 breast cancer cell lines.

Authors:  K Nagaiah; A Venkatesham; R Srinivasa Rao; V Saddanapu; J S Yadav; S J Basha; A V S Sarma; B Sridhar; A Addlagatta
Journal:  Bioorg Med Chem Lett       Date:  2010-04-18       Impact factor: 2.823

2.  On the nature of organic catalysis "on water".

Authors:  Yousung Jung; R A Marcus
Journal:  J Am Chem Soc       Date:  2007-03-28       Impact factor: 15.419

Review 3.  Organic reactions on silica in water.

Authors:  Satoshi Minakata; Mitsuo Komatsu
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

4.  One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multicomponent reactions and their molecular switching properties.

Authors:  Kuan-Ting Li; Yong-Bo Lin; Ding-Yah Yang
Journal:  Org Lett       Date:  2012-02-14       Impact factor: 6.005

5.  An efficient tandem approach for the synthesis of functionalized 2-pyridone-3-carboxylic acids using three-component reaction in aqueous media.

Authors:  Saber Mehrparvar; Saeed Balalaie; Mahnaz Rabbanizadeh; Elmira Ghabraie; Frank Rominger
Journal:  Mol Divers       Date:  2014-05-04       Impact factor: 2.943

6.  Design, synthesis and evaluation of cytotoxicity of novel chromeno[4,3-b]quinoline derivatives.

Authors:  Ramin Miri; Radineh Motamedi; Mohammad Reza Rezaei; Omidreza Firuzi; Azita Javidnia; Abbas Shafiee
Journal:  Arch Pharm (Weinheim)       Date:  2010-11-18       Impact factor: 3.751

7.  ERbeta ligands. Part 6: 6H-Chromeno[4,3-b]quinolines as a new series of estrogen receptor beta-selective ligands.

Authors:  An T Vu; Alison N Campbell; Heather A Harris; Rayomand J Unwalla; Eric S Manas; Richard E Mewshaw
Journal:  Bioorg Med Chem Lett       Date:  2007-05-04       Impact factor: 2.823

8.  Synthesis and biological activity of 5-methylidene 1,2-dihydrochromeno[3,4-f]quinoline derivatives as progesterone receptor modulators.

Authors:  Lin Zhi; Christopher M Tegley; Barbara Pio; James P Edwards; Todd K Jones; Keith B Marschke; Dale E Mais; Boris Risek; William T Schrader
Journal:  Bioorg Med Chem Lett       Date:  2003-06-16       Impact factor: 2.823

Review 9.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

10.  Potent anti-inflammatory effects of two quinolinedione compounds, OQ1 and OQ21, mediated by dual inhibition of inducible NO synthase and cyclooxygenase-2.

Authors:  Kyung-Min Lim; Joo-Young Lee; Song-Mi Lee; Ok-Nam Bae; Ji-Yoon Noh; Eun-Jin Kim; Seung-Min Chung; Jin-Ho Chung
Journal:  Br J Pharmacol       Date:  2009-01-19       Impact factor: 8.739
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  2 in total

Review 1.  Multicomponent Reactions Accelerated by Aqueous Micelles.

Authors:  Daniel Paprocki; Arleta Madej; Dominik Koszelewski; Anna Brodzka; Ryszard Ostaszewski
Journal:  Front Chem       Date:  2018-10-22       Impact factor: 5.221

Review 2.  Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone.

Authors:  S S Shatokhin; V A Tuskaev; S Ch Gagieva; É T Oganesyan
Journal:  Russ Chem Bull       Date:  2021-07-14       Impact factor: 1.222
  2 in total

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