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Synthesis 2020; 52(15): 2196-2223
DOI: 10.1055/s-0039-1690833
DOI: 10.1055/s-0039-1690833
paper
Application of the Intramolecular Diels–Alder Vinylarenе (IMDAV) Approach for the Synthesis of Thieno[2,3-f]isoindoles
Funding for this research was provided by the Ministry of Education and Science of the Russian Federation (award no. 4.1154.2017/4.6). DFT calculation part of this work has been supported by the Fundação para a Ciência e a Tecnologia (FCT), Portugal, project UIDB/00100/2020 of Centro de Química Estrutural.Further Information
Publication History
Received: 11 December 2019
Accepted after revision: 31 January 2020
Publication Date:
12 March 2020 (online)
Abstract
3-(Thien-2-yl)- and 3-(thien-3-yl)allylamines, readily accessible from the corresponding thienyl aldehydes, can interact with a broad range of anhydrides and α,β-unsaturated acids chlorides (maleic, сitraconic, and phenyl maleic anhydrides, сrotonyl and сinnamyl chlorides, etc.) leading to the formation of a thieno[2,3-f]isoindole core. Usually, the reaction sequence involves three successive steps: acylation of the nitrogen atom of the initial allylamine, the intramolecular Diels–Alder vinylarenе (IMDAV) reaction, and the final aromatization of the dihydrothiophene ring in the Diels–Alder adducts. The scope and limitations of the proposed method were thoroughly investigated. It was revealed with the aid of X-ray analysis that the key step, the IMDAV reaction, proceeds through an exo-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. In the case of maleic anhydrides, the method allows to obtain functionally substituted thieno[2,3-f]isoindole carboxylic acids, which are potentially useful substrates for further transformations and subsequent bioscreening.
Key words
intramolecular Diels–Alder reaction - vinylarenеs - IMDAV reaction - thieno[2,3-f]isoindole - thiophene - tandem reaction - intramolecular [4+2] cycloadditionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690833.
- Supporting Information
- CIF File
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Computational details: Full geometry optimization of all structures and transition states was carried out at the DFT level of theory by using the M06-2X functional, see:
The 6-311++G** basis was set with the help of the Gaussian 09 program package: