Literature DB >> 32457563

Regioselective Alkylation of Pyridinium Riboses.

Farbod Salahi1, Olaf Wiest1.   

Abstract

The nucleophilic addition of alkyl, benzyl, and allyl organozinc reagents to protected pyridinium riboses proceeds under mild conditions and with yields of >90% in several cases and complete regioselectivity for the 4-position.

Entities:  

Keywords:  Alkylation; Allylation; Nitrogen heterocycles; Nucleophilic addition; Synthetic methods

Year:  2019        PMID： 32457563      PMCID： PMC7250371          DOI： 10.1002/ejoc.201901603

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  13 in total

Review 1.  Synthesis of pyridine and dihydropyridine derivatives by regio- and stereoselective addition to N-activated pyridines.

Authors:  James A Bull; James J Mousseau; Guillaume Pelletier; André B Charette
Journal:  Chem Rev       Date:  2012-02-21       Impact factor: 60.622

2.  Synthesis of the isonicotinoylnicotinamide scaffolds of the naturally occurring isoniazid-NAD(P) adducts.

Authors:  Tamara Delaine; Vania Bernardes-Génisson; Bernard Meunier; Jean Bernadou
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

3.  Transition-metal-free BF3-mediated regioselective direct alkylation and arylation of functionalized pyridines using Grignard or organozinc reagents.

Authors:  Quan Chen; Xavier Mollat du Jourdin; Paul Knochel
Journal:  J Am Chem Soc       Date:  2013-03-26       Impact factor: 15.419

4.  Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis.

Authors:  D A Rozwarski; G A Grant; D H Barton; W R Jacobs; J C Sacchettini
Journal:  Science       Date:  1998-01-02       Impact factor: 47.728

5.  Development of isoniazid-NAD truncated adducts embedding a lipophilic fragment as potential bi-substrate InhA inhibitors and antimycobacterial agents.

Authors:  Tamara Delaine; Vania Bernardes-Génisson; Annaïk Quémard; Patricia Constant; Bernard Meunier; Jean Bernadou
Journal:  Eur J Med Chem       Date:  2010-07-15       Impact factor: 6.514

6.  Highly functionalized organomagnesium reagents prepared through halogen-metal exchange.

Authors:  Paul Knochel; Wolfgang Dohle; Nina Gommermann; Florian F Kneisel; Felix Kopp; Tobias Korn; Ioannis Sapountzis; Viet Anh Vu
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-22       Impact factor: 15.336

7.  Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile.

Authors:  Michael W Gribble; Sheng Guo; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-04-06       Impact factor: 15.419

8.  Cardioprotective activity of a novel and potent competitive inhibitor of lactate dehydrogenase.

Authors:  Alexander B Kotlyar; Antonio Randazzo; Norman Honbo; Zhu-Qui Jin; Joel S Karliner; Gary Cecchini
Journal:  FEBS Lett       Date:  2010-01-04       Impact factor: 4.124

9.  In vitro inhibition of the Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein reductase MabA by isoniazid.

Authors:  Stéphanie Ducasse-Cabanot; Martin Cohen-Gonsaud; Hedia Marrakchi; Michel Nguyen; Didier Zerbib; Jean Bernadou; Mamadou Daffé; Gilles Labesse; Annaïk Quémard
Journal:  Antimicrob Agents Chemother       Date:  2004-01       Impact factor: 5.191

10.  Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling.

Authors:  Eugenio Gandolfo; Xinjun Tang; Sudipta Raha Roy; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-07       Impact factor: 15.336
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