The intramolecular Diels-Alder vinylthiophen (IMDAV) reaction: An easy approach to thieno[2,3-f]isoindole-4-carboxylic acids |
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Authors: | Yuriy I Horak Roman Z Lytvyn Yevhen-Oleh V Laba Yuriy V Homza Vladimir P Zaytsev Maryana A Nadirova Tatiana V Nikanorova Fedor I Zubkov Alexey V Varlamov Mykola D Obushak |
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Institution: | 1. Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine;2. Department of Organic Chemistry, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation |
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Abstract: | The reaction of readily accessible 3-(thien-2-yl)allylamines with maleic anhydride, followed by a domino sequence involving successive acylation/4+2] cycloaddition steps, leads to the formation of the thieno2,3-f]isoindole core. The key step, the intramolecular Diels-Alder vinylaren (IMDAV) reaction, proceeds with high level of diastereoselectivity and with formation of a single diastereoisomer of the target product 4,4a,5,6,7,7a-hexahydro-3aH-thieno2,3-f]isoindole-4-carboxylic acids in excellent yields. If the reaction is carried out at room temperature, it occurs in 2–3 days and the proton migration (H-shift) does not take place at the last stage. In boiling benzene, the reaction is complete after three hours, but in this case a slight impurity of byproducts bearing aromatic thiophene ring – 4a,5,6,7,7a,8-hexahydro-4H-thieno2,3-f]isoindole-4-carboxylic acids is formed. |
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Keywords: | Vinylthiophene [4+2] cycloaddition Intramolecular Diels-Alder reaction IMDAV reaction Thiophene |
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