Application of the Intramolecular Didehydro-Diels–Alder (IMDDA) Reaction for the Synthesis of Thieno[2,3-f]isoindole-4(8)-carboxylic Acids
Abstract The reaction of 3-(thienyl)propargylamines with maleic anhydride, followed by a domino sequence involving successive acylation/[4+2] cycloaddition steps, leads to the formation of the thieno[2,3-f]isoindole core. The key step, the intramolecular didehydro-Diels–Alder (IMDDA) reaction, proceeds with a high level of selectivity, yielding the target products – 7-oxo-5,6,7,8-tetrahydro-4H-thieno[2,3-f]isoindole-4(8)-carboxylic acids – in good yields. X-ray analysis and DFT calculations have revealed that the key step, the IMDDA reaction, proceeds via an exo transition allene state, resulting in the exclusive formation of a single isomer of the target heterocycle.
Authors
- N. A. Logvinenko (ORCID: https://orcid.org/0000-0001-8564-7353)
- Федор И. Зубков (ORCID: https://orcid.org/0000-0002-0289-0831)
- Evgeniya R. Shelukho (ORCID: https://orcid.org/0000-0003-1310-6536)
- Victor N. Khrustalev (ORCID: https://orcid.org/0000-0001-8806-2975)
- Vladimir P. Zaytsev (ORCID: https://orcid.org/0000-0001-9175-7583)
- Роман А. Новиков (ORCID: https://orcid.org/0000-0002-3740-7424)
- Elizaveta D. Yakovleva (ORCID: https://orcid.org/0000-0002-8819-4043)
Institutions
- Engelhardt Institute of Molecular Biology (RU)
- Peoples' Friendship University of Russia (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
Publication Details
- Journal
- Synlett
- Published
- 2025-05-06
- DOI
- https://doi.org/10.1055/s-0043-1773527
- Citations
- 1
- Primary Topic
- Synthesis and pharmacology of benzodiazepine derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Russian Science Foundation