Intramolecular Photochemical Cross-Coupling Reactions of 3-Acyl-2-haloindoles and 2-Chloropyrrole-3-carbaldehydes with Substituted Benzenes

Authors

  • Shen-Ci Lu,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-891-2582
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  • Xi-Xia Zhang,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-891-2582
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  • Zong-Jun Shi,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-891-2582
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  • Yu-Wei Ren,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-891-2582
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  • Bing Li,

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-891-2582
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  • Wei Zhang

    1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China, Fax: (+86)-931-891-2582
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Abstract

Highly efficient syntheses of indolo[2,1-a]isoquinolines, indolo[2,1-a][2]benzazepines, pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]benzazepines in excellent yields have been achieved by the intramolecular photochemical cross-coupling reactions of 3-acyl-2-halo-N-(ω-arylalkyl)indoles and 2-chloro-N-(ω-arylalkyl)pyrrole-3-carbaldehydes in acetone. A new heterocyclic ring system – pyrrolo[1,2-d][1,4]benzoxazepine – has also been constructed for the first time in this work by the photocyclization of 2-chloro-N-(2-phenoxyethyl)pyrrole-3-carbaldehyde.

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