Literature DB >> 22765354

Palladium-catalyzed N-monoarylation of amidines and a one-pot synthesis of quinazoline derivatives.

Meredeth A McGowan1, Camille Z McAvoy, Stephen L Buchwald.   

Abstract

A method for the Pd-catalyzed N-arylation of both aryl and alkyl amidines with a wide range of aryl bromides, chlorides, and triflates is described. The reactions proceed in short reaction times and with excellent selectivity for monoarylation. A one-pot synthesis of quinazoline derivatives, via addition of an aldehyde to the crude reaction mixture following Pd-catalyzed N-arylation, is also demonstrated.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22765354      PMCID： PMC3485433          DOI： 10.1021/ol301700y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  C-H functionalization/C-N bond formation: copper-catalyzed synthesis of benzimidazoles from amidines.

Authors:  Gordon Brasche; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Palladium-catalyzed intramolecular C(sp2)-H amidination by isonitrile insertion provides direct access to 4-aminoquinazolines from N-arylamidines.

Authors:  Yong Wang; Honggen Wang; Jiangling Peng; Qiang Zhu
Journal:  Org Lett       Date:  2011-08-05       Impact factor: 6.005

3.  NOpiates: Novel Dual Action Neuronal Nitric Oxide Synthase Inhibitors with μ-Opioid Agonist Activity.

Authors:  Paul Renton; Brenda Green; Shawn Maddaford; Suman Rakhit; John S Andrews
Journal:  ACS Med Chem Lett       Date:  2012-01-30       Impact factor: 4.345

4.  Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

Authors:  Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-18       Impact factor: 15.336

5.  Synthesis and pharmacological evaluation of 1H-imidazoles as ligands for the estrogen receptor and cytotoxic inhibitors of the cyclooxygenase.

Authors:  Thomas Wiglenda; Ingo Ott; Brigitte Kircher; Petra Schumacher; Daniela Schuster; Thierry Langer; Ronald Gust
Journal:  J Med Chem       Date:  2005-10-06       Impact factor: 7.446

Review 6.  Transition metal-catalyzed N-arylations of amidines and guanidines.

Authors:  Tom R M Rauws; Bert U W Maes
Journal:  Chem Soc Rev       Date:  2012-01-05       Impact factor: 54.564

7.  Synthesis of symmetrical and unsymmetrical N,N'-diaryl guanidines via copper/N-methylglycine-catalyzed arylation of guanidine nitrate.

Authors:  Hui Xing; Ye Zhang; Yisheng Lai; Yongwen Jiang; Dawei Ma
Journal:  J Org Chem       Date:  2012-06-07       Impact factor: 4.354

8.  An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides.

Authors:  Brett P Fors; Karin Dooleweerdt; Qingle Zeng; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

9.  Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation.

Authors:  Takashi Ikawa; Timothy E Barder; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

10.  Copper-catalyzed synthesis of benzimidazoles via cascade reactions of o-haloacetanilide derivatives with amidine hydrochlorides.

Authors:  Daoshan Yang; Hua Fu; Liming Hu; Yuyang Jiang; Yufen Zhao
Journal:  J Org Chem       Date:  2008-08-28       Impact factor: 4.354
View more
  8 in total

1.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

Review 2.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

3.  Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes.

Authors:  Kaj M van Vliet; Lara H Polak; Maxime A Siegler; Jarl Ivar van der Vlugt; Célia Fonseca Guerra; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2019-09-10       Impact factor: 15.419

4.  Catalyst-free one-pot, four-component approach for the synthesis of di- and tri-substituted N-sulfonyl formamidines.

Authors:  Ai-Ran Liu; Lei Zhang; Jiao Li; Abudureheman Wusiman
Journal:  RSC Adv       Date:  2021-04-27       Impact factor: 3.361

5.  Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp3)-H amidination.

Authors:  Dianke Xie; Wei He; Jiang Xiao; Yao Wu; Yongjia Guo; Qiang Liu; Cancheng Guo
Journal:  RSC Adv       Date:  2019-03-04       Impact factor: 4.036

6.  Quinazoline derivatives: synthesis and bioactivities.

Authors:  Dan Wang; Feng Gao
Journal:  Chem Cent J       Date:  2013-06-03       Impact factor: 4.215

7.  Decarboxylative palladium(II)-catalyzed synthesis of aryl amidines from aryl carboxylic acids: development and mechanistic investigation.

Authors:  Jonas Rydfjord; Fredrik Svensson; Alejandro Trejos; Per J R Sjöberg; Christian Sköld; Jonas Sävmarker; Luke R Odell; Mats Larhed
Journal:  Chemistry       Date:  2013-08-28       Impact factor: 5.236

8.  Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites.

Authors:  Jack Robertson; Marzuq A Ungogo; Mustafa M Aldfer; Leandro Lemgruber; Fergus S McWhinnie; Bela E Bode; Katherine L Jones; Allan J B Watson; Harry P de Koning; Glenn A Burley
Journal:  ChemMedChem       Date:  2021-09-02       Impact factor: 3.540
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.