A Five-Step Cascade for the Modular and Regiodefined Synthesis of Naphth[2,1-d]oxazoles

Dinda, Bidyut Kumar; Basak, Shyam; Ghosh, B. N.; Mal, Dipakranjan

doi:10.1055/s-0035-1561376

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Cited by 9 publications

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Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura Annulations

Koning¹,

Georgiou²,

Michael³

et al. 2021

Organic Reactions

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This chapter provides a detailed survey of the Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura annulation reactions, as reported in the literature through March 2021. These reactions provide an efficient means for the synthesis of polycyclic aromatic compounds and related systems. The mechanism, scope, and limitations of each annulation reaction are covered, and typical methods for the preparation of the requisite starting materials (phthalides, homophthalic anhydrides, and related precursors) are provided. Applications of these annulation reactions as key steps in the synthesis of selected aromatic natural products are included, as are representative experimental procedures for accomplishing the annulation reactions.

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Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura Annulations

Koning¹,

Georgiou²,

Michael³

et al. 2021

Organic Reactions

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Synthesis of Sulfonyloxindoles via Functional Group Exchange Between 3‐Sulfonylphthalide and Isatylidenemalononitrile

2021

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An unusual reactivity of 3-sulfonylphthalides with isatylidenemalononitriles has been exploited to provide an efficient entry into 3-sulfonyloxindoles. Although a Hauser-Kraus mechanism can be visualized for the observed transformation, a more probable mechanism, based on control experiments and spectroscopic studies, involves Michael addition of sulfonylphthalide to isatylidenemalononitrile followed by elimination and re-addition of sulfonyl and malononitrile functionalities in an overall functional group exchange between phthalide and oxindolyl moieties. We have also demonstrated the synthetic applications of the sulfonyloxindoles in selected reactions such as conjugate addition and aromatization.

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