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Literature DB >> 23999797

Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones.

Alexander V Aksenov¹, Alexander N Smirnov, Nicolai A Aksenov, Inna V Aksenova, Liliya V Frolova, Alexander Kornienko, Igor V Magedov, Michael Rubin.

Abstract

3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.

Entities: Chemical Disease Species

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Year: 2013 PMID： 23999797 PMCID： PMC4945960 DOI： 10.1039/c3cc45696j

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

18 in total

Review 1. Practical methodologies for the synthesis of indoles.

Authors: Guy R Humphrey; Jeffrey T Kuethe
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

2. 3-Aryl-4-methyl-2-quinolones targeting multiresistant Staphylococcus aureus bacteria.

Authors: Anne Doléans-Jordheim; Jean-Baptiste Veron; Olivier Fendrich; Emmanuelle Bergeron; Adrien Montagut-Romans; Yung-Sing Wong; Bianca Furdui; Jean Freney; Charles Dumontet; Ahcène Boumendjel
Journal: ChemMedChem Date: 2013-02-21 Impact factor: 3.466

3. Facile and efficient synthesis of quinolin-2(1H)-ones via cyclization of penta-2,4-dienamides mediated by H2SO4.

Authors: Xu Liu; Xin Xin; Dexuan Xiang; Rui Zhang; Santosh Kumar; Fenguo Zhou; Dewen Dong
Journal: Org Biomol Chem Date: 2012-06-25 Impact factor: 3.876

4. An investigation into the structure-activity relationships associated with the systematic modification of the β(2)-adrenoceptor agonist indacaterol.

Authors: David Beattie; David Beer; Michelle E Bradley; Ian Bruce; Steven J Charlton; Bernard M Cuenoud; Robin A Fairhurst; David Farr; John R Fozard; Diana Janus; Elizabeth M Rosethorne; David A Sandham; David A Sykes; Alexandre Trifilieff; Katharine L Turner; Elke Wissler
Journal: Bioorg Med Chem Lett Date: 2012-08-04 Impact factor: 2.823

5. Design and synthesis of 3-(4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)-1H-quinolin-2-ones as VEGFR-2 kinase inhibitors.

Authors: Sun-Young Han; Jie Won Choi; Jeon Yang; Chong Hack Chae; Jongkook Lee; Heejung Jung; Kwangho Lee; Jae Du Ha; Hyoung Rae Kim; Sung Yun Cho
Journal: Bioorg Med Chem Lett Date: 2012-03-07 Impact factor: 2.823

6. Elucidation of structure-activity relationship of 2-quinolone derivatives and exploration of their antitumor potential through Bax-induced apoptotic pathway.

Authors: Nitesh Kumar; Vasanth P Raj; B S Jayshree; Sidhartha S Kar; Arvind Anandam; Seeja Thomas; Prateek Jain; Amita Rai; C M Rao
Journal: Chem Biol Drug Des Date: 2012-06-06 Impact factor: 2.817

Review 7. Heterocycles as nonclassical bioisosteres of α-amino acids.

Authors: Christian B M Poulie; Lennart Bunch
Journal: ChemMedChem Date: 2013-01-15 Impact factor: 3.466

8. 4H-1,2-benzoxazines with electron-withdrawing substituents on the benzene ring: synthesis and application as potent intermediates for oxygen-functionalized aromatic compounds.

Authors: Satoshi Nakamura; Masanobu Uchiyama; Tomohiko Ohwada
Journal: J Am Chem Soc Date: 2003-05-07 Impact factor: 15.419

9. Cascade palladium-catalyzed alkenyl aminocarbonylation/ intramolecular aryl amidation: an annulative synthesis of 2-quinolones.

Authors: Andrew C Tadd; Ai Matsuno; Mark R Fielding; Michael C Willis
Journal: Org Lett Date: 2009-02-05 Impact factor: 6.005

10. Discovery of (R)-N-(3-(7-methyl-1H-indazol-5-yl)-1-(4-(1-methylpiperidin-4-yl)-1-oxopropan-2-yl)-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide (BMS-742413): a potent human CGRP antagonist with superior safety profile for the treatment of migraine through intranasal delivery.

Authors: Prasad V Chaturvedula; Stephen E Mercer; Sokhom S Pin; George Thalody; Cen Xu; Charlie M Conway; Deborah Keavy; Laura Signor; Glenn H Cantor; Neil Mathias; Paul Moench; Rex Denton; Robert Macci; Richard Schartman; Valerie Whiterock; Carl Davis; John E Macor; Gene M Dubowchik
Journal: Bioorg Med Chem Lett Date: 2013-04-12 Impact factor: 2.823

5 in total

1. Activity of 2-aryl-2-(3-indolyl)acetohydroxamates against drug-resistant cancer cells.

Authors: Alexander V Aksenov; Alexander N Smirnov; Igor V Magedov; Mary R Reisenauer; Nicolai A Aksenov; Inna V Aksenova; Alexander L Pendleton; Gina Nguyen; Robert K Johnston; Michael Rubin; Annelise De Carvalho; Robert Kiss; Véronique Mathieu; Florence Lefranc; Jaime Correa; David A Cavazos; Andrew J Brenner; Brad A Bryan; Snezna Rogelj; Alexander Kornienko; Liliya V Frolova
Journal: J Med Chem Date: 2015-02-20 Impact factor: 7.446

Review 2. Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid.

Authors: Elida N Thobokholt; Enrique L Larghi; Andrea B J Bracca; Teodoro S Kaufman
Journal: RSC Adv Date: 2020-05-19 Impact factor: 4.036