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[3+2] Cycloaddition of o-nitrophenyl azide to 3a,6-epoxyisoindoles

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Chemistry of Heterocyclic Compounds Aims and scope

[3+2] Cycloaddition of o-nitrophenyl azide to the multiple bond of oxabicyclo[2.2.1]heptene moiety in substituted 3a,6-epoxyisoindoles was performed. The 1,3-dipolar addition reaction proceeded stereoselectively, producing a pair of isomeric cis-4,8a-epoxy[1,2,3]triazolo[4,5-e]isoindoles. This approach demonstrated synthetic access to isomeric epoxy-1,2,3-benzotriazoles fused with a γ-butyrolactam moiety.

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The synthesis of starting isoindoles 2–5 was performed with financial support from the Russian Foundation for Basic Research (grant 16-33-00389), the synthesis of triazoles 6 and X-ray structural analyses received support from the Ministry of Education and Science of the Russian Federation (project 4.1154.2017/4.6).

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Authors and Affiliations

  1. RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Vladimir P. Zaytsev, Dmitriy F. Mertsalov, Maryana A. Nadirova, Victor N. Khrustalev, Elena A. Sorokina, Fedor I. Zubkov & Aleksey V. Varlamov

  2. National Research Center “Kurchatov Institute”, 1 Akademika Kurchatova Sq., Moscow, 123182, Russia

    Pavel V. Dorovatovskii

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  1. Vladimir P. Zaytsev
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  2. Dmitriy F. Mertsalov
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  3. Maryana A. Nadirova
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  4. Pavel V. Dorovatovskii
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  5. Victor N. Khrustalev
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  6. Elena A. Sorokina
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  7. Fedor I. Zubkov
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  8. Aleksey V. Varlamov
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Correspondence to Vladimir P. Zaytsev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, Submitted June 22, 2017 2017, 53(11), 1199–1206

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Zaytsev, V.P., Mertsalov, D.F., Nadirova, M.A. et al. [3+2] Cycloaddition of o-nitrophenyl azide to 3a,6-epoxyisoindoles. Chem Heterocycl Comp 53, 1199–1206 (2017). https://doi.org/10.1007/s10593-018-2194-1

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