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Application of the Intramolecular Diels–Alder Vinylarenе (IMDAV) Approach for the Synthesis of Thieno[2,3-f]isoindoles
Synthesis ( IF 2.2 ) Pub Date : 2020-03-12 , DOI: 10.1055/s-0039-1690833 Mykola D. Obushak 1 , Fedor I. Zubkov 2 , Maryana A. Nadirova 2 , Yevhen-Oleh V. Laba 1 , Vladimir P. Zaytsev 2 , Julya S. Sokolova 2 , Kuzma M. Pokazeev 2 , Victoria A. Anokhina 2 , Victor N. Khrustalev 2, 3 , Yuriy I. Horak 1 , Roman Z. Lytvyn 1 , Miłosz Siczek 4 , Vasyl Kinzhybalo 5 , Yan V. Zubavichus 6 , Maxim L. Kuznetsov 7
Synthesis ( IF 2.2 ) Pub Date : 2020-03-12 , DOI: 10.1055/s-0039-1690833 Mykola D. Obushak 1 , Fedor I. Zubkov 2 , Maryana A. Nadirova 2 , Yevhen-Oleh V. Laba 1 , Vladimir P. Zaytsev 2 , Julya S. Sokolova 2 , Kuzma M. Pokazeev 2 , Victoria A. Anokhina 2 , Victor N. Khrustalev 2, 3 , Yuriy I. Horak 1 , Roman Z. Lytvyn 1 , Miłosz Siczek 4 , Vasyl Kinzhybalo 5 , Yan V. Zubavichus 6 , Maxim L. Kuznetsov 7
Affiliation
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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.
中文翻译：
分子内Diels–AlderVinylarenе（IMDAV）方法在噻吩并[2,3-f]异吲哚的合成中的应用
很容易从相应的噻吩基醛中获得的3-（噻吩-2-基）-和3-（噻吩-3-基）烯丙胺可以与各种酸酐和α，β-不饱和酰氯（马来酸，顺丁烯二酸）相互作用，以及苯基马来酸酐，叔丁酰和肉桂酰氯等），导致形成噻吩并[2,3- f ]异吲哚核。通常，反应顺序包括三个连续的步骤：初始烯丙胺的氮原子的酰化，分子内Diels-Alder乙烯基芳烃（IMDAV）反应以及Diels-Alder加合物中二氢噻吩环的最终芳构化。彻底研究了该方法的范围和局限性。借助X射线分析表明，关键步骤IMDAV反应通过exo进行。-过渡态，引起目标杂环的单一非对映异构体的排他形成。在马来酸酐的情况下，该方法允许获得官能取代的噻吩并[2,3- f ]异吲哚羧酸，其对于进一步转化和随后的生物筛选是潜在有用的底物。
更新日期：2020-03-12
中文翻译：
分子内Diels–AlderVinylarenе（IMDAV）方法在噻吩并[2,3-f]异吲哚的合成中的应用
很容易从相应的噻吩基醛中获得的3-（噻吩-2-基）-和3-（噻吩-3-基）烯丙胺可以与各种酸酐和α，β-不饱和酰氯（马来酸，顺丁烯二酸）相互作用，以及苯基马来酸酐，叔丁酰和肉桂酰氯等），导致形成噻吩并[2,3- f ]异吲哚核。通常，反应顺序包括三个连续的步骤：初始烯丙胺的氮原子的酰化，分子内Diels-Alder乙烯基芳烃（IMDAV）反应以及Diels-Alder加合物中二氢噻吩环的最终芳构化。彻底研究了该方法的范围和局限性。借助X射线分析表明，关键步骤IMDAV反应通过exo进行。-过渡态，引起目标杂环的单一非对映异构体的排他形成。在马来酸酐的情况下，该方法允许获得官能取代的噻吩并[2,3- f ]异吲哚羧酸，其对于进一步转化和随后的生物筛选是潜在有用的底物。
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