Application of the Intramolecular Diels-Alder Vinylarenе (IMDAV) Approach for the Synthesis of Thieno[2,3-f[isoindoles

3-(Thien-2-yl)- A nd 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, N itraconic-, and phenyl maleic anhydrides, N rotonyl and N innamyl 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. © 2020 Georg Thieme Verlag. All rights reserved.

Nadirova M.A. 1 , Laba Y.-O.V.2 , Zaytsev V.P. 1 , Sokolova J.S. 1 , Pokazeev K.M. 1 , Anokhina V.A. 1 , Khrustalev V.N. 1, 7 , Horak Y.I. 2 , Lytvyn R.Z. 2 , Siczek M.3 , Kinzhybalo V.4 , Zubavichus Y.V. 5 , Kuznetsov M.L.6 , Obushak M.D. 2 , Zubkov F.I. 1
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  • 1 Peoples' Friendship University of Russia, RUDN University, 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 2 Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv, 79005, Ukraine
  • 3 Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, Wrocław, 50-383, Poland
  • 4 Institute of Low Temperature and Structure Research, PAS, Okólna 2, Wrocław, 50-422, Poland
  • 5 National Research Centre 'Kurchatov Institute', Moscow, 123182, Russian Federation
  • 6 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon, 1049-001, Portugal
  • 7 Zelinsky Institute of Organic Chemistry, RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation
Ключевые слова
IMDAV reaction; intrac-molecular [4+2] cycloaddition; Intramolecular Diels-Alder reaction; tandem reaction; thieno[2,3-f[isoindole; thiophene; vinylarenеs
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