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Paper | Regular issue | Vol 43, No. 9, 1996, pp.1959-1966
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7533
Formation of a Ten-membered Lactam by Chloroacetamide Photocyclization on the Indole 4-Position

M.-LLuïsa Bennasar, Ester Zulaica, Antonio Ramírez, and Joan Bosch*

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain


Photocyclization of tricyclic chloroacetamide (3) occurs on the indole 4-position to give the ten-membered lactam (4), whose structure was confirmed by conversion to the tetracyclic amine (6). Some conformational aspects of lactam (4) and thiolactam (5), namely the observation of conformers by nmr as a consequence of a restricted inversion of the ten-membered ring, are discussed.