Literature DB >> 22845666

Iron-catalyzed formation of 2-aminopyridines from diynes and cyanamides.

Timothy K Lane1, Brendan R D'Souza, Janis Louie.   

Abstract

Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively.

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Year:  2012        PMID: 22845666      PMCID: PMC3480319          DOI: 10.1021/jo3012418

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


  39 in total

1.  Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.

Authors:  Jesús A Varela; Carlos Saá
Journal:  Chem Rev       Date:  2003-09       Impact factor: 60.622

2.  Silylstannylation of highly functionalized acetylenes. synthesis of precursors for annulations via radical or Heck reactions.

Authors:  Sandeep Apte; Branko Radetich; Seunghoon Shin; T V RajanBabu
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

3.  Synthesis of aminopyridines and aminopyridones by cobalt-catalyzed [2+2+2] cycloadditions involving yne-ynamides: scope, limitations, and mechanistic insights.

Authors:  Pierre Garcia; Yannick Evanno; Pascal George; Mireille Sevrin; Gino Ricci; Max Malacria; Corinne Aubert; Vincent Gandon
Journal:  Chemistry       Date:  2012-03-01       Impact factor: 5.236

4.  Fused phenanthridines: domino cyclization of 1,6-diynes with bromo(iso)quinoline.

Authors:  Yimin Hu; Yongjie Sun; Jiping Hu; Tao Zhu; Tao Yu; Quansheng Zhao
Journal:  Chem Asian J       Date:  2011-01-11

5.  Iron-catalyzed cycloaddition of alkynenitriles and alkynes.

Authors:  Brendan R D'Souza; Timothy K Lane; Janis Louie
Journal:  Org Lett       Date:  2011-05-10       Impact factor: 6.005

6.  Cobalt-catalyzed alkyne-nitrile cyclotrimerization to form pyridines in aqueous solution.

Authors:  A W Fatland; B E Eaton
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

7.  Intramolecular cyclotrimerization of triynes catalyzed by N-heterocyclic carbene-CoCl2/Zn or -FeCl3/Zn.

Authors:  Naoko Saino; Daisuke Kogure; Sentaro Okamoto
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

8.  A mechanistic dichotomy in ruthenium-catalyzed propargyl alcohol reactivity: a novel hydrative diyne cyclization.

Authors:  Barry M Trost; Michael T Rudd
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

9.  An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.

Authors:  Ryan A Altman; Alexandr Shafir; Alice Choi; Phillip A Lichtor; Stephen L Buchwald
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354

10.  Structure-activity relationship of bromoeudistomin D, a powerful Ca2+ releaser in skeletal muscle sarcoplasmic reticulum.

Authors:  Y Takahashi; K Furukawa; M Ishibashi; D Kozutsumi; H Ishiyama; J Kobayashi; Y Ohizumi
Journal:  Eur J Pharmacol       Date:  1995-02-15       Impact factor: 4.432

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  4 in total

1.  The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.

Authors:  Timothy K Lane; Minh H Nguyen; Brendan R D'Souza; Nathan A Spahn; Janis Louie
Journal:  Chem Commun (Camb)       Date:  2013-09-11       Impact factor: 6.222

Review 2.  Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion.

Authors:  Alois Fürstner
Journal:  ACS Cent Sci       Date:  2016-10-27       Impact factor: 14.553

Review 3.  Recent Advances in Cyanamide Chemistry: Synthesis and Applications.

Authors:  M R Ranga Prabhath; Luke Williams; Shreesha V Bhat; Pallavi Sharma
Journal:  Molecules       Date:  2017-04-12       Impact factor: 4.411

Review 4.  Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4-8 transition metal catalysts.

Authors:  Daniel N Huh; Yukun Cheng; Connor W Frye; Dominic T Egger; Ian A Tonks
Journal:  Chem Sci       Date:  2021-06-29       Impact factor: 9.825

  4 in total

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