Literature DB >> 21732649

Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines.

Ryan E Looper1, Travis J Haussener, James B C Mack.   

Abstract

A simple and efficient one-pot method for the synthesis of monoprotected guanidines is presented. Treatment of an acylcyanamide with chlorotrimethylsilane generates a reactive N-silylcarbodiimide capable of guanylating a variety of amines. Typically the reaction is complete in 15 min for primary and secondary aliphatic amines at rt. Hindered amines and anilines are also competent nucleophiles but require extended reaction times.

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Year:  2011        PMID： 21732649      PMCID： PMC3189699          DOI： 10.1021/jo201264j

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


  13 in total

1.  Solid-phase synthesis of N-acyl-N'-alkyl/aryl disubstituted guanidines.

Authors:  A K Ghosh; W G Hol; E Fan
Journal:  J Org Chem       Date:  2001-03-23       Impact factor: 4.354

2.  Solution-phase, parallel synthesis and pharmacological evaluation of acylguanidine derivatives as potential sodium channel blockers.

Authors:  S Padmanabhan; R C Lavin; P M Thakker; J Guo; L Zhang; D Moore; M E Perlman; C Kirk; D Daly; K J Burke-Howie; T Wolcott; S Chari; D Berlove; J B Fischer; W F Holt; G J Durant; R N McBurney
Journal:  Bioorg Med Chem Lett       Date:  2001-12-17       Impact factor: 2.823

3.  Asymmetric total synthesis of batzelladine D.

Authors:  F Cohen; L E Overman; S K Sakata
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Review 4.  Noncovalent binding between guanidinium and anionic groups: focus on biological- and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues.

Authors:  Kevin A Schug; Wolfgang Lindner
Journal:  Chem Rev       Date:  2005-01       Impact factor: 60.622

5.  Enantioselective synthesis of alpha-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst.

Authors:  E J Corey; M J Grogan
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

6.  Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4 + 2]-annulation of vinyl carbodiimides with N-alkyl imines.

Authors:  Michael A Arnold; Kenneth A Day; Sergio G Durón; David Y Gin
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

7.  (5-Arylfuran-2-ylcarbonyl)guanidines as cardioprotectives through the inhibition of Na+/H+ exchanger isoform-1.

Authors:  Sunkyung Lee; Kyu Yang Yi; Sun Kyung Hwang; Byung Ho Lee; Sung-Eun Yoo; Kyunghee Lee
Journal:  J Med Chem       Date:  2005-04-21       Impact factor: 7.446

Review 8.  Molecular recognition of oxoanions based on guanidinium receptors.

Authors:  Pascal Blondeau; Margarita Segura; Ruth Pérez-Fernández; Javier de Mendoza
Journal:  Chem Soc Rev       Date:  2006-11-09       Impact factor: 54.564

9.  Direct synthesis of bicyclic guanidines through unprecedented palladium(ii) catalysed diamination with copper chloride as oxidant.

Authors:  Claas H Hövelmann; Jan Streuff; Lydia Brelot; Kilian Muñiz
Journal:  Chem Commun (Camb)       Date:  2008-03-14       Impact factor: 6.222

10.  Expanding the substrate scope for C-H amination reactions: oxidative cyclization of urea and guanidine derivatives.

Authors:  Mihyong Kim; John V Mulcahy; Christine G Espino; J Du Bois
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005
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  10 in total

1.  Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Authors:  Artur K Mailyan; Kyle Young; Joanna L Chen; Bradley T Reid; Armen Zakarian
Journal:  Org Lett       Date:  2016-10-25       Impact factor: 6.005

2.  Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation.

Authors:  Bradley T Reid; Artur K Mailyan; Armen Zakarian
Journal:  J Org Chem       Date:  2018-06-22       Impact factor: 4.354

3.  Syntheses of Cyclic Guanidine-Containing Natural Products.

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Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

4.  A simple method for the electrophilic cyanation of secondary amines.

Authors:  Chen Zhu; Ji-Bao Xia; Chuo Chen
Journal:  Org Lett       Date:  2013-12-06       Impact factor: 6.005

5.  Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines.

Authors:  Justin M Salvant; Anne V Edwards; Daniel Z Kurek; Ryan E Looper
Journal:  J Org Chem       Date:  2017-06-15       Impact factor: 4.354

6.  Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.

Authors:  Joseph B Gibbons; Justin M Salvant; Rachel M Vaden; Ki-Hyeok Kwon; Bryan E Welm; Ryan E Looper
Journal:  J Org Chem       Date:  2015-09-24       Impact factor: 4.354

7.  A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products.

Authors:  Christopher E Malmberg; Stephen Chamberland
Journal:  J Vis Exp       Date:  2016-09-09       Impact factor: 1.355

8.  Synthesis of bicyclic guanidines via cascade hydroamination/Michael additions of mono-N-acryloylpropargylguanidines.

Authors:  Ki-Hyeok Kwon; Catherine M Serrano; Michael Koch; Louis R Barrows; Ryan E Looper
Journal:  Org Lett       Date:  2014-11-13       Impact factor: 6.005

9.  Axinellamines as broad-spectrum antibacterial agents: scalable synthesis and biology.

Authors:  Rodrigo A Rodriguez; Danielle Barrios Steed; Yu Kawamata; Shun Su; Peter A Smith; Tyler C Steed; Floyd E Romesberg; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-10-20       Impact factor: 15.419

10.  11-Step Total Synthesis of Araiosamines.

Authors:  Maoqun Tian; Ming Yan; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-10-19       Impact factor: 15.419
  10 in total

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