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

Maryana A. Nadirova; Yevhen-Oleh V. Laba; Vladimir P. Zaytsev; Julya S. Sokolova; Kuzma M. Pokazeev; Victoria A. Anokhina; Victor N. Khrustalev; Yuriy I. Horak; Roman Z. Lytvyn; Miłosz Siczek; Vasyl Kinzhybalo; Yan V. Zubavichus; Maxim L. Kuznetsov; Mykola D. Obushak; Fedor I. Zubkov

doi:10.1055/s-0039-1690833

Synthesis, Table of Contents

Synthesis 2020; 52(15): 2196-2223
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

Maryana A. Nadirova

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

,

Yevhen-Oleh V. Laba

^bIvan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine

,

Vladimir P. Zaytsev

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

,

Julya S. Sokolova

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

,

Kuzma M. Pokazeev

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

,

Victoria A. Anokhina

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

,

Victor N. Khrustalev

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

^gZelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow 119991, Russian Federation

,

Yuriy I. Horak

^bIvan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine

,

Roman Z. Lytvyn

^bIvan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine

,

Miłosz Siczek

^cFaculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland Email: milosz.siczek@uwr.edu.pl

,

Vasyl Kinzhybalo

^dInstitute of Low Temperature and Structure Research, PAS, Okólna 2, 50-422 Wrocław, Poland Email: kinzhybalo@gmail.com

,

Yan V. Zubavichus

^eNational Research Centre ‘Kurchatov Institute’, Moscow 123182, Russian Federation

,

Maxim L. Kuznetsov

^fCentro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon 1049-001, Portugal Email: max@mail.ist.utl.pt

,

Mykola D. Obushak∗

^bIvan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine

,

Fedor I. Zubkov ∗

^aPeoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation Email: fzubkov@sci.pfu.edu.ru

› Author Affiliations

Abstract

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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] cycloaddition

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References

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