Literature DB >> 24313859

A simple method for the electrophilic cyanation of secondary amines.

Chen Zhu1, Ji-Bao Xia, Chuo Chen.   

Abstract

Bleach oxidizes trimethylsilyl cyanide to generate an electrophilic cyanating reagent that readily reacts with an amine nucleophile. This oxidative N-cyanation reaction allows for the preparation of disubstituted cyanamides from amines without using highly toxic cyanogen halides.

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Year:  2013        PMID： 24313859      PMCID： PMC3907775          DOI： 10.1021/ol403245r

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


  21 in total

1.  Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors:  Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

2.  [2-(4-Phenyl-4-piperidinyl)ethyl]amine based CCR5 antagonists: derivatizations at the N-terminal of the piperidine ring.

Authors:  Maosheng Duan; Christopher Aquino; Robert Ferris; Wieslaw M Kazmierski; Terry Kenakin; Cecilia Koble; Pat Wheelan; Chris Watson; Michael Youngman
Journal:  Bioorg Med Chem Lett       Date:  2009-02-10       Impact factor: 2.823

3.  Cyanamide synthesis by the palladium-catalyzed cleavage of a Si-N bond.

Authors:  Shin Kamijo; Tienan Jin; Yoshinori Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

4.  N-Bromosuccinimide promoted one-pot synthesis of guanidine: scope and mechanism.

Authors:  Ling Zhou; Jie Chen; Jing Zhou; Ying-Yeung Yeung
Journal:  Org Lett       Date:  2011-10-11       Impact factor: 6.005

5.  Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.

Authors:  Ryan M Stolley; Michael T Maczka; Janis Louie
Journal:  European J Org Chem       Date:  2011-07

6.  Radical synthesis of guanidines from N-acyl cyanamides.

Authors:  Marie-Hélène Larraufie; Cyril Ollivier; Louis Fensterbank; Max Malacria; Emmanuel Lacôte
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-15       Impact factor: 15.336

7.  A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

Authors:  Ji-Bao Xia; Kevin W Cormier; Chuo Chen
Journal:  Chem Sci       Date:  2012-04-13       Impact factor: 9.825

8.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

9.  Catalytic asymmetric mannich-type reactions activated by ZnF2 chiral diamine in aqueous media.

Authors:  Tomoaki Hamada; Kei Manabe; Shū Kobayashi
Journal:  Chemistry       Date:  2006-01-23       Impact factor: 5.236

10.  Synthesis and structure-activity studies of N,N'-diarylguanidine derivatives. N-(1-naphthyl)-N'-(3-ethylphenyl)-N'-methylguanidine: a new, selective noncompetitive NMDA receptor antagonist.

Authors:  N L Reddy; L Y Hu; R E Cotter; J B Fischer; W J Wong; R N McBurney; E Weber; D L Holmes; S T Wong; R Prasad
Journal:  J Med Chem       Date:  1994-01-21       Impact factor: 7.446
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  3 in total

Review 1.  Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

Authors:  Lifen Peng; Zhifang Hu; Hong Wang; Li Wu; Yinchun Jiao; Zilong Tang; Xinhua Xu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

Review 2.  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

3.  SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN).

Authors:  Yiyong Zhao; Junjie Wei; Shuting Ge; Guofu Zhang; Chengrong Ding
Journal:  RSC Adv       Date:  2020-05-04       Impact factor: 4.036
  3 in total

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