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Synthesis 2021; 53(02): 296-308
DOI: 10.1055/s-0040-1707318
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Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals

Milene Macedo Hornink
,
Alice Uva Lopes
,
Leandro Helgueira Andrade  ∗
We thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (National Council for Scientific and Technological Development, CNPq, grant no. 312751/2018-4), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (Coordination for the Improvement of Higher Education Personnel, CAPES), and Fundação de Amparo à Pesquisa do Estado de São Paulo (The São Paulo Research Foundation, FAPESP, grant nos. 2017/02854-8, 2018/07152-4, and 2019/10762-1) for financial support.
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Abstract

Spiroimides exhibit a wide range of biological activities, such as anticonvulsant, antiarrhythmic, and antihyperglycemic activities. Herein, a novel synthetic application of renewable chemicals, itaconic acid and formamides, is described. Proper exploitation of the reactivity of itaconic acid and formamide allows for the development of an efficient synthetic approach for the production of several new biobased spiroimides, spiro[dihydroquinolin-2-one-succinimides] and spiro[indolin-2-one-glutarimides], in excellent overall yields (up to 98%).

Key words

spiroimides - itaconic acid - formamides - renewable building blocks - photochemistry

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707318.
  • Supporting Information


Publication History

Received: 17 June 2020

Accepted after revision: 08 September 2020

Article published online:
20 October 2020

© 2020. Thieme. All rights reserved

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