Literature DB >> 23301562

Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

Xinfang Xu1, Peter Y Zavalij, Wenhao Hu, Michael P Doyle.   

Abstract

A regiospecific synthesis of multifunctional pyrazoleshas been developed from a cascade process triggered by Rh(II)-catalyzed dinitrogen extrusion from enol diazoacetates with vinylogous nucleophilic addition followed by Lewis acid catalyzed cyclization and aromatization.

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Year:  2013        PMID： 23301562      PMCID： PMC3574190          DOI： 10.1021/jo302696y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  60 in total

1.  Diverse trifluoromethyl heterocycles from a single precursor.

Authors:  Mark A Honey; Raffaele Pasceri; William Lewis; Christopher J Moody
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2.  A modular sydnone cycloaddition/Suzuki-Miyaura cross-coupling strategy to unsymmetrical 3,5-bis(hetero)aromatic pyrazoles.

Authors:  Thierry Delaunay; Pierre Genix; Mazen Es-Sayed; Jean-Pierre Vors; Nuno Monteiro; Geneviève Balme
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

3.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

4.  Pyrazole and pyrimidine phenylacylsulfonamides as dual Bcl-2/Bcl-xL antagonists.

Authors:  Gretchen M Schroeder; Donna Wei; Patrizia Banfi; Zhen-Wei Cai; Jonathan Lippy; Maria Menichincheri; Michele Modugno; Joseph Naglich; Becky Penhallow; Heidi L Perez; John Sack; Robert J Schmidt; Andrew Tebben; Chunhong Yan; Liping Zhang; Arturo Galvani; Louis J Lombardo; Robert M Borzilleri
Journal:  Bioorg Med Chem Lett       Date:  2012-04-30       Impact factor: 2.823

5.  A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence.

Authors:  R U Braun; K Zeitler; T J Müller
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

6.  1,3-Dipolar cycloaddition reactions of vinylidenecyclopropane-diesters with aromatic diazomethanes generated in situ.

Authors:  Lei Wu; Min Shi
Journal:  J Org Chem       Date:  2010-04-02       Impact factor: 4.354

7.  Cooperative catalysis in highly enantioselective Mannich-type three-component reaction of a diazoacetophenone with an alcohol and an imine.

Authors:  Xinfang Xu; Yu Qian; Liping Yang; Wenhao Hu
Journal:  Chem Commun (Camb)       Date:  2010-11-29       Impact factor: 6.222

8.  Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs.

Authors:  Jill Arrowsmith; Sharon A Jennings; Alan S Clark; Malcolm F G Stevens
Journal:  J Med Chem       Date:  2002-12-05       Impact factor: 7.446

9.  Enantioselective conjugate addition of donor-acceptor hydrazones to α,β-unsaturated aldehydes through formal diaza-ene reaction: access to 1,4-dicarbonyl compounds.

Authors:  Maitane Fernández; Uxue Uria; Jose L Vicario; Efraím Reyes; Luisa Carrillo
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419

10.  Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: development of central cannabinoid receptor ligands with lower lipophilicity.

Authors:  Reeti Katoch-Rouse; Olga A Pavlova; Tara Caulder; Alexander F Hoffman; Alexey G Mukhin; Andrew G Horti
Journal:  J Med Chem       Date:  2003-02-13       Impact factor: 7.446
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  7 in total

1.  Rh2(R-TPCP)4-catalyzed enantioselective [3+2]-cycloaddition between nitrones and vinyldiazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2013-09-20       Impact factor: 15.419

2.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

Review 3.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

4.  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Authors:  Paul A Allegretti; Khoi Huynh; Tarik J Ozumerzifon; Eric M Ferreira
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

5.  Silver-catalyzed vinylogous fluorination of vinyl diazoacetates.

Authors:  Changming Qin; Huw M L Davies
Journal:  Org Lett       Date:  2013-11-14       Impact factor: 6.005

6.  The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Authors:  Xinfang Xu; Michael P Doyle
Journal:  Acc Chem Res       Date:  2014-03-20       Impact factor: 22.384

7.  Carbene-catalyzed enantioselective annulation of dinucleophilic hydrazones and bromoenals for access to aryl-dihydropyridazinones and related drugs.

Authors:  Bivas Mondal; Rakesh Maiti; Xing Yang; Jun Xu; Weiyi Tian; Jia-Lei Yan; Xiangyang Li; Yonggui Robin Chi
Journal:  Chem Sci       Date:  2021-05-17       Impact factor: 9.825
  7 in total

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