4.5 Review

Dimroth's Rearrangement as a Synthetic Strategy Towards New Heterocyclic Compounds

Journal

CURRENT ORGANIC CHEMISTRY
Volume 24, Issue 17, Pages 1999-2018

Publisher

BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1385272824999200805114837

Keywords

Heterocycles; synthesis; azoles; 1,2,3-triazoles; pyrimidine; quinazoline

Funding

  1. Fundacao Carlos Chagas Filho de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ) [E-26/010.101106/2018, E-26/202.800/2017]
  2. Conselho Nacional de Desenvolvimento Cientifico e Tecnologic (CNPq) [301873/2019-4]
  3. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) [001, Print 88881.310204/2018-01]

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Molecular rearrangements are important tools to increase the molecular diversity of new bioactive compounds, especially in the class of heterocycles. This review deals specifically with a very famous and widely applicable rearrangement known as the Dimroth Rearrangement. Although it has originally been observed for 1,2,3-triazoles, its amplitude was greatly expanded to other heterocycles, as well as from laboratory to large scale production of drugs and intermediates. The reactions that were discussed in this review were selected with the aim of demonstrating the windows that may be open by the Dimroth's rearrangement, especially in what regards the development of new synthetic approaches toward biologically active compounds.

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