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Photochemistry of Benzotriazoles: Generation of 1,3-Diradicals and Intermolecular Cycloaddition as a New Route toward Indoles and Dihydropyrrolo[3,4-b]Indoles

Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
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Molecules 2014, 19(12), 20695-20708; https://doi.org/10.3390/molecules191220695
Received: 4 November 2014 / Revised: 26 November 2014 / Accepted: 27 November 2014 / Published: 11 December 2014
(This article belongs to the Section Organic Chemistry)
Irradiation of benzotriazoles 1ae at λ = 254 nm in acetonitrile solution generated the corresponding 1,3-diradicals which underwent intermolecular cycloaddition with maleimides to afford the corresponding dihydropyrrolo[3,4-b]indoles and with acetylene derivatives to afford indoles as the major products. This offers an interesting and simple access to such ring systems of potential synthetic and biological interest. The structures of the photoproducts were established spectroscopically and by single crystal X-ray crystallography. View Full-Text
Keywords: photolysis; benzotriazoles; maleimides; alkynes; indoles; pyrrolo[3,4-b]indoles photolysis; benzotriazoles; maleimides; alkynes; indoles; pyrrolo[3,4-b]indoles
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Al-Jalal, N.A.; Ibrahim, M.R.; Al-Awadi, N.A.; Elnagdi, M.H.; Ibrahim, Y.A. Photochemistry of Benzotriazoles: Generation of 1,3-Diradicals and Intermolecular Cycloaddition as a New Route toward Indoles and Dihydropyrrolo[3,4-b]Indoles. Molecules 2014, 19, 20695-20708.

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