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Synthesis 1986; 1986(9): 748-749
DOI: 10.1055/s-1986-31763
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Synthesis and [4 + 2]-Cycloadditions of N-Phenylsulfonyl-3-vinylindole

B. Saroja* , P. C. Srinivasan
  • *Department of Organic Chemistry, University of Madras, Madras - 600 025, India
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Publication Date:
20 August 2002 (online)

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1-Phenylsulfonyl-3-vinylindole can be prepared in good yield from the 3-ethyl derivative by a two-step bromination dehydrobromination sequence, As a 1,3-diene it undergoes [4+2]-cycloadditions with N-phenylmaleimide, p-benzoquinone, and dialkyl acetylenedicarboxylates to give derivatives of the 1,2,3,3a,4,5,10,10b-octahydropyrrolo[3,4-a]carbazole, 1,4,4a,5,6,11b-hexahydro-11H-benzo[a]carbazole, and carbazole ring systems, respectively.

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