Literature DB >> 26366017

Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-alkylation/tandem cyclization.

Huy H Nguyen1, James C Fettinger1, Makhluf J Haddadin2, Mark J Kurth1.   

Abstract

A transition metal-free, one-pot protocol has been developed for the synthesis of 11H-indolo[3,2-c]isoquinolin-5-amines via the atom economical annulation of ethyl (2-cyanophenyl)carbamates and 2-cyanobenzyl bromides. This method proceeds via sequential N-alkylation and base-promoted cyclization. Optimization data, substrate scope, mechanistic insights, and photoluminescence properties are discussed.

Entities:  

Keywords:  domino process; indolo[3,2-c]isoquinoline; one-pot; photoluminescence; tandem cyclization

Year:  2015        PMID： 26366017      PMCID： PMC4564870          DOI： 10.1016/j.tetlet.2015.08.006

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

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Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Synthesis and antimalarial evaluation of novel isocryptolepine derivatives.

Authors:  Louise R Whittell; Kevin T Batty; Rina P M Wong; Erin M Bolitho; Simon A Fox; Timothy M E Davis; Paul E Murray
Journal:  Bioorg Med Chem       Date:  2011-10-20       Impact factor: 3.641

Review 3.  Multi-component syntheses of heterocycles by transition-metal catalysis.

Authors:  Daniel M D'Souza; Thomas J J Müller
Journal:  Chem Soc Rev       Date:  2007-02-19       Impact factor: 54.564

4.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

5.  The antimalarial and cytotoxic drug cryptolepine intercalates into DNA at cytosine-cytosine sites.

Authors:  John N Lisgarten; Miquel Coll; Jose Portugal; Colin W Wright; Juan Aymami
Journal:  Nat Struct Biol       Date:  2002-01

6.  Synthesis and evaluation of cryptolepine analogues for their potential as new antimalarial agents.

Authors:  C W Wright; J Addae-Kyereme; A G Breen; J E Brown; M F Cox; S L Croft; Y Gökçek; H Kendrick; R M Phillips; P L Pollet
Journal:  J Med Chem       Date:  2001-09-13       Impact factor: 7.446

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Authors:  I K Sawer; M I Berry; M W Brown; J L Ford
Journal:  J Appl Bacteriol       Date:  1995-09

8.  Studies on cryptolepine. Cryptolepine antagonism of noradrenaline and modification of this effect by calcium ions and prostaglandin E2 on rat isolated mesenteric artery.

Authors:  B K Noamesi; S O Bamgbose
Journal:  Planta Med       Date:  1983-02       Impact factor: 3.352

9.  Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds.

Authors:  James D Sunderhaus; Stephen F Martin
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

10.  Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

Authors:  Huy H Nguyen; Mark J Kurth
Journal:  Org Lett       Date:  2012-12-26       Impact factor: 6.005
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  2 in total

1.  An efficient solvent-free synthesis of 2-(alkylamino)-2-oxo-1-arylethyl-6,12-dioxo-6,12-dihydroindolo[1,2-b]isoquinoline-11-carboxylate derivatives via four-component reaction.

Authors:  Tahmineh Kenarkoohi; Abbas Rahmati
Journal:  Mol Divers       Date:  2019-01-05       Impact factor: 2.943

2.  Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli-Cushman Precursor.

Authors:  Elizaveta Karchuganova; Olga Bakulina; Dmitry Dar'in; Mikhail Krasavin
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411
  2 in total

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