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

Molecules

Nader A. Al-Jalal¹  Maher R. Ibrahim²  Nouria A. Al-Awadi²  Mohamed H. Elnagdi²  Yehia A. Ibrahim² 

[1] Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait;

关键词: photolysis;    benzotriazoles;    maleimides;    alkynes;    indoles;    pyrrolo[3;    4-b]indoles;   

DOI  :  10.3390/molecules191220695

来源: mdpi

【 摘 要 】

Irradiation of benzotriazoles 1a–e 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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.