Literature DB >> 19341310

Mild and efficient DBU-catalyzed amidation of cyanoacetates.

Kristin E Price1, Claude Larrivée-Aboussafy, Brett M Lillie, Robert W McLaughlin, Jason Mustakis, Kevin W Hettenbach, Joel M Hawkins, Rajappa Vaidyanathan.   

Abstract

A mild, high-yielding, and practical protocol for the direct amidation of alkyl cyanoacetates using DBU is presented. This method eliminates the need for activation of cyanoacetic acid and/or high temperatures. It has been applied to the large-scale synthesis of CP-690,550-10 (1), a compound under development for the treatment of autoimmune diseases.

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Year:  2009        PMID： 19341310     DOI： 10.1021/ol900435t

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


  10 in total

1.  Optimized 5-membered heterocycle-linked pterins for the inhibition of Ricin Toxin A.

Authors:  Jeff M Pruet; Ryota Saito; Lawrence A Manzano; Karl R Jasheway; Paul A Wiget; Ishan Kamat; Eric V Anslyn; Jon D Robertus
Journal:  ACS Med Chem Lett       Date:  2012-05-29       Impact factor: 4.345

2.  Cyanoacetamides (IV): versatile one-pot route to 2-quinoline-3-carboxamides.

Authors:  Kan Wang; Eberhardt Herdtweck; Alexander Dömling
Journal:  ACS Comb Sci       Date:  2012-04-18       Impact factor: 3.784

3.  Peptide-conjugated pterins as inhibitors of ricin toxin A.

Authors:  Ryota Saito; Jeff M Pruet; Lawrence A Manzano; Karl Jasheway; Arthur F Monzingo; Paul A Wiget; Ishan Kamat; Eric V Anslyn; Jon D Robertus
Journal:  J Med Chem       Date:  2012-12-19       Impact factor: 7.446

4.  p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates.

Authors:  Madhuri Vangala; Ganesh P Shinde
Journal:  Beilstein J Org Chem       Date:  2016-09-26       Impact factor: 2.883

Review 5.  Inside Perspective of the Synthetic and Computational Toolbox of JAK Inhibitors: Recent Updates.

Authors:  Adriana Coricello; Francesco Mesiti; Antonio Lupia; Annalisa Maruca; Stefano Alcaro
Journal:  Molecules       Date:  2020-07-22       Impact factor: 4.411

6.  Exploring the scope of DBU-promoted amidations of 7-methoxycarbonylpterin.

Authors:  Anna R Bockman; Jeffrey M Pruet
Journal:  Beilstein J Org Chem       Date:  2020-03-26       Impact factor: 2.883

7.  Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines.

Authors:  Sergey A Rzhevskiy; Alexandra A Ageshina; Gleb A Chesnokov; Pavel S Gribanov; Maxim A Topchiy; Mikhail S Nechaev; Andrey F Asachenko
Journal:  RSC Adv       Date:  2019-01-11       Impact factor: 4.036

8.  6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis.

Authors:  Takeshi Yamada; Yusuke Watanabe; Sentaro Okamoto
Journal:  RSC Adv       Date:  2021-07-14       Impact factor: 4.036

9.  Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters.

Authors:  Blessing D Mkhonazi; Malibongwe Shandu; Ronewa Tshinavhe; Sandile B Simelane; Paseka T Moshapo
Journal:  Molecules       Date:  2020-02-26       Impact factor: 4.411

10.  Synthesis and characterization of dendritic compounds containing nitrogen: monomer precursors in the construction of biomimetic membranes.

Authors:  Jordi Guardià; Alireza Zare; John Eleeza; Marta Giamberini; José Antonio Reina; Xavier Montané
Journal:  Sci Rep       Date:  2022-02-02       Impact factor: 4.379
  10 in total

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