Literature DB >> 18345680

One-pot three-component synthesis of alpha-iminonitriles by IBX/TBAB-mediated oxidative Strecker reaction.

Patrice Fontaine1, Angèle Chiaroni, Géraldine Masson, Jieping Zhu.   

Abstract

The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded alpha-iminonitriles in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodology was applied to a two-step synthesis of indolizidine via a microwave-assisted intramolecular cycloaddition of alpha-iminonitrile.

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Year:  2008        PMID: 18345680     DOI: 10.1021/ol800199b

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


  6 in total

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Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

2.  Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Authors:  Naveen R Rondla; Jodi M Ogilvie; Zhongda Pan; Christopher J Douglas
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3.  Room-temperature aromatization of tetrahydro-β-carbolines by 2-iodoxybenzoic acid: utility in a total synthesis of eudistomin U.

Authors:  Joseph D Panarese; Stephen P Waters
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

4.  Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers.

Authors:  Prakash Basnet; Melissa B Sebold; Charles E Hendrick; Marisa C Kozlowski
Journal:  Org Lett       Date:  2020-12-02       Impact factor: 6.005

5.  A truly green synthesis of α-aminonitriles via Strecker reaction.

Authors:  Debasish Bandyopadhyay; Juliana M Velazquez; Bimal K Banik
Journal:  Org Med Chem Lett       Date:  2011-10-04

6.  From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of C(sp3)-H Bond.

Authors:  Huiwen Chi; Hao Li; Bingxin Liu; Rongxuan Ye; Haoyang Wang; Yin-Long Guo; Qitao Tan; Bin Xu
Journal:  iScience       Date:  2019-11-01
  6 in total

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