Hauser-Kraus Annulation of Phthalides with Nitroalkenes for the Synthesis of Fused and Spiro Heterocycles

Kumar, Tarun ; Satam, Nishikant ; Namboothiri, Irishi N. N. (2016) Hauser-Kraus Annulation of Phthalides with Nitroalkenes for the Synthesis of Fused and Spiro Heterocycles European Journal of Organic Chemistry, 2016 (20). pp. 3316-3321. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201600390

Related URL: http://dx.doi.org/10.1002/ejoc.201600390

Abstract

Hauser–Kraus annulation of sulfonylphthalides with simple conjugated nitroalkenes follows the expected pathway to furnish naphthoquinones in moderate yields. However, a strategic variation of this reaction by employing nitroalkenes bearing an additional nucleophilic site results in [4+4] annulation leading to complex fused and spiro heterocycles in high yields with high selectivity through a cascade process involving Michael addition, Dieckmann cyclization, and a series of eliminations and rearrangements.

Item Type:Article
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ID Code:121324
Deposited On:14 Jul 2021 09:57
Last Modified:14 Jul 2021 09:57

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