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3+2] CYCLOADDITION OF o-NITROPHENYL AZIDE TO 3а,6-EPOXYISOINDOLES

Владимир Петрович Зайцев, Дмитрий Федорович Мерцалов, Марианна Албертовна Надирова, Павел Дороватовский, Виктор Николаевич Хрусталёв, Елена Анатольевна Сорокина, Федор Иванович Зубков, Алексей Васильевич Варламов
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Abstract


[3+2] Cycloaddition of о-nitrophenyl azide to the multiple bond of oxabicyclo[2.2.1]heptene moiety in substituted 3а,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.

 


Keywords


1,2,3-benzotriazoles, 3а,6-epoxyisoindoles, 4,8a-epoxy[1,2,3]triazolo[4,5-e]isoindoles, о-nitrophenyl azide, [3+2] cycloaddition, 1,3-dipolar cycloaddition.

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