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DOI: 10.1055/s-0040-1705983
IntraMolecular Diels–Alder Reactions of Vinylarenes and Alkynyl Arenes (the IMDAV Reaction)
Funding for this research was provided by the Ministry of Education and Science of the Russian Federation [Award no. 075-03-2020-223 (FSSF-2020-0017)]. G.K. declares that Section 7 of this publication was prepared with the support of RUDN University ‘Program 5-100’.
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Abstract
This comprehensive review summarizes the published literature data concerning the intramolecular Diels–Alder reactions of vinylarenes (the IMDAV reaction) and alkynyl arenes from 1970 to 2019, and covers mainly intramolecular [4+2] cycloaddition reactions of vinyl- or acetylene-substituted furans, thiophenes, pyrroles, indoles, imidazoles, benzenes, and naphthalenes, in which the unsaturated substituent is linked directly to an arene moiety. The selected area of the Diels–Alder reaction differs from other forms of [4+2] cycloadditions due to the uniqueness of the diene fragment, which, along with an exocyclic multiple bond, includes the double bond of an aromatic or heteroaromatic nucleus in its system. Thus, during the formation of the [4+2] cycloaddition intermediate, the aromaticity of furan, thiophene and even benzene rings is broken, leading, as a rule, to the formation of heterocyclic structures rarely accessible by other methods, in contrast to the majority of intermolecular Diels–Alder reactions, with the highest degree of chemo-, regio-, and diastereoselectivity. Therefore, the IMDAV approach is often used for the synthesis of naturally occurring and bioactive molecules, which are also discussed in this review alongside other applications of this reaction. Whenever possible, we have tried to avoid examples of radical, photochemical, oxidative, precious-metal-complex-catalyzed cyclizations and other types of formal [4+2] cycloadditions, focusing on thermal Diels–Alder reactions in the first step, according to the classical mechanism. The second stage of the process, aromatization, is unique for many initial substrates, and hence considerable attention in this overview is given to the detailed description of the reaction mechanisms.
1 Introduction
2 IMDAV Reactions of Vinylfurans
2.1 Alkenes as Internal Dienophiles
2.2 Alkynes and Allenes as Internal Dienophiles
3 IMDAV Reactions of Vinylthiophenes
3.1 Alkenes as Internal Dienophiles
3.2 Alkynes as Internal Dienophiles
4 IMDAV Reactions of Vinylbenzothiophenes
5 IMDAV Reactions of Vinylpyrroles
6 IMDAV Reactions of Vinylindoles
6.1 Alkenes as Internal Dienophiles
6.2 Alkynes as Internal Dienophiles
7 IMDAV Reactions of Styrenes and Vinylnaphthalenes
7.1 Alkenes as Internal Dienophiles
7.2 Alkynes as Internal Dienophiles
7.3 Alkynes as Internal Dienophiles in Aryl Acetylenes (the Intramolecular Dehydro Diels–Alder Reaction)
8 IMDAV Reactions of Vinylimidazoles, Vinylisoxazoles and Vinylpyridines
9 Conclusion
10 Abbreviations
Key words
IMDAV reaction - intramolecular [4+2] cycloaddition - intramolecular Diels–Alder reaction - vinylarenes - аlkynyl arenes - dienophiles - alkenesPublikationsverlauf
Eingereicht: 11. September 2020
Angenommen nach Revision: 20. Oktober 2020
Artikel online veröffentlicht:
14. Januar 2021
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For very recent work regarding kinetic and thermodynamic control in intramolecular Diels–Alder reactions, see:
For details on the isolation, biochemical properties and chemistry of these lignans, see: