IntraMolecular Diels–Alder Reactions of Vinylarenes and Alkynyl Arenes (the IMDAV Reaction)

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 - alkenes

Publication History

Received: 11 September 2020

Accepted after revision: 20 October 2020

Article published online:
14 January 2021

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