Literature DB >> 24989674

Regiocontrolled gold-catalyzed [2+2+2] cycloadditions of ynamides with two discrete nitriles to construct 4-aminopyrimidine cores.

Somnath Narayan Karad1, Rai-Shung Liu.   

Abstract

Reported herein is the novel gold-catalyzed intermolecular [2+2+2] cycloaddition of ynamides with two discrete nitriles to form monomeric 4-aminopyrimidines, which are pharmaceutically important structural motifs. The utility of this new cycloaddition is demonstrated by the excellent regioselectivity obtained using a variety of ynamides and nitriles.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloadditions; gold; heterocycles; homogeneous catalysis; synthetic methods

Year:  2014        PMID： 24989674     DOI： 10.1002/anie.201405312

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  Oxidative Coupling with Zr(IV) Supported by a Noninnocent Anthracene-Based Ligand: Application to the Catalytic Cotrimerization of Alkynes and Nitriles to Pyrimidines.

Authors:  Choon Heng Low; Jeffrey N Rosenberg; Marco A Lopez; Theodor Agapie
Journal:  J Am Chem Soc       Date:  2018-09-14       Impact factor: 15.419

2.  A Silver(I)-Catalyzed Intramolecular Ficini's [2 + 2] Cycloaddition Employing Ynamides.

Authors:  Xiao-Na Wang; Zhi-Xiong Ma; Jun Deng; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  A Scalable Synthesis of the Difluoromethyl-allo-threonyl Hydroxamate-Based LpxC Inhibitor LPC-058.

Authors:  Xiaofei Liang; Ramesh Gopalaswamy; Frank Navas; Eric J Toone; Pei Zhou
Journal:  J Org Chem       Date:  2016-05-06       Impact factor: 4.354

4.  Ynamide carbopalladation: a flexible route to mono-, bi- and tricyclic azacycles.

Authors:  Craig D Campbell; Rebecca L Greenaway; Oliver T Holton; P Ross Walker; Helen A Chapman; C Adam Russell; Greg Carr; Amber L Thomson; Edward A Anderson
Journal:  Chemistry       Date:  2015-07-16       Impact factor: 5.236

5.  Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans.

Authors:  Hélio Faustino; Iván Varela; José L Mascareñas; Fernando López
Journal:  Chem Sci       Date:  2015-03-02       Impact factor: 9.825

6.  Temperature controlled condensation of nitriles: efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system.

Authors:  Yinghua Li; Yingzu Zhu; Shiqun Xiang; Weibin Fan; Jiang Jin; Deguang Huang
Journal:  RSC Adv       Date:  2020-02-12       Impact factor: 3.361

7.  Metal-free intermolecular formal cycloadditions enable an orthogonal access to nitrogen heterocycles.

Authors:  Lan-Gui Xie; Supaporn Niyomchon; Antonio J Mota; Leticia González; Nuno Maulide
Journal:  Nat Commun       Date:  2016-03-15       Impact factor: 14.919

8.  Gold-catalyzed formal [4π + 2π]-cycloadditions of propiolate derivatives with unactivated nitriles.

Authors:  Somnath Narayan Karad; Wei-Kang Chung; Rai-Shung Liu
Journal:  Chem Sci       Date:  2015-07-20       Impact factor: 9.825

9.  Annulation cascade of arylnitriles with alkynes to stable delocalized PAH carbocations via intramolecular rhodium migration.

Authors:  Jiangliang Yin; Fulin Zhou; Lei Zhu; Mufan Yang; Yu Lan; Jingsong You
Journal:  Chem Sci       Date:  2018-05-29       Impact factor: 9.825

10.  Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N→3/C-Sulfonyl Migration.

Authors:  Ivan Bernar; Daniel Blanco-Ania; Sophie J Stok; Lia Sotorríos; Enrique Gómez-Bengoa; Floris P J T Rutjes
Journal:  European J Org Chem       Date:  2018-10-10
  10 in total

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