Literature DB >> 20527906

Facile double-lithiation of a transient urea: vicarious ortho-metalation of aniline derivatives.

Chris E Houlden1, Guy C Lloyd-Jones, Kevin I Booker-Milburn.   

Abstract

A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithio-phenylisocyanate, a highly improbable intermediate.

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Year:  2010        PMID： 20527906     DOI： 10.1021/ol101102y

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


  3 in total

1.  Exploring a sulfone linker utilizing trimethyl aluminum as a cleavage reagent: solid-phase synthesis of sulfonamides and ureas.

Authors:  Tsai-Wen Chung; Chih-Hau Chen; Chu-Chung Lin; Hsien-Jen Wu; Chung-Ming Sun; Wen-Sheng Chung
Journal:  Mol Divers       Date:  2012-06-30       Impact factor: 2.943

2.  A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas.

Authors:  Keith Smith; Gamal A El-Hiti; Amany S Hegazy; Benson Kariuki
Journal:  Beilstein J Org Chem       Date:  2011-09-06       Impact factor: 2.883

3.  Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones.

Authors:  Marie Vayer; Miryam Pastor; Christiane Kofink; Nuno Maulide
Journal:  Org Lett       Date:  2021-12-24       Impact factor: 6.005
  3 in total

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