title: Photochemistry of benzotriazoles: generation of 1,3-diradicals and intermolecular cycloaddition as a new route toward indoles and dihydropyrrolo[3,4-b]indoles.
abstract: 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.
authors.affiliation: Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. nader.aljalal@ku.edu.kw.
authors.forename: Nader A
authors.initials: NA
authors.lastname: Al-Jalal
authors.affiliation: Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. maherriyad@hotmail.com.
authors.forename: Maher R
authors.initials: MR
authors.lastname: Ibrahim
authors.affiliation: Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. n.alawadi@ku.edu.kw.
authors.forename: Nouria A
authors.initials: NA
authors.lastname: Al-Awadi
authors.affiliation: Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. shelmy1941@yahoo.com.
authors.forename: Mohamed H
authors.initials: MH
authors.lastname: Elnagdi
authors.affiliation: Department of Chemistry, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. yehiaibrahim2002@yahoo.com.
authors.forename: Yehia A
authors.initials: YA
authors.lastname: Ibrahim
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D005609:Free Radicals / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D010782:Photolysis; D012997:Solvents / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000097:Acetonitriles; D005609:Free Radicals; D007211:Indoles; D012997:Solvents; D014230:Triazoles; C012771:benzotriazole; C032159:acetonitrile