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Paper | Regular issue | Vol 53, No. 2, 2000, pp.277-290
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8737
Novel Indole-fused, Medium-sized Ring Heterocycles via Chloroacetamide Photochemistry

John B. Bremner,* Henry F. Russell, Brian W. Skelton, and Allan H. White

*Department of Chemistry, University of Wollongong, Wollongong 2522 NSW, Australia


Syntheses of derivatives of three novel indole-fused systems based on indolo[2,1-d][1,5]benzodiazocine, indolo[7,7a,1-d,e][1,6]benzodiazonine and pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline, the first two including 8- and 9-membered ring heterocycles, are described. These derivatives resulted from the photo-induced cyclization of the respective chloroacetamide precursors prepared via N-alkylation of the appropriate indole with 2-nitrobenzyl bromide, subsequent nitro group reduction and then N-chloroacetylation. Structural and stereochemical features of these new ring system derivatives are discussed.