Abstract
An efficient one-pot procedure is described in which an isocyanate
intermediate, generated from the corresponding carboxylic acid by
a modified Curtius rearrangement, is captured by a tethered aromatic
ring in the presence of BF3 ˙OEt2 to
generate various lactams, including tetrahydro-β-carbolin-1-one
and dihydroisoquinolin-1-one derivatives.
Key words
cyclizations - heterocycles - lactams - Lewis
acids - rearrangements
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54 Crystallographic data for compounds 1a and 2d have
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supplementary publications CCDC 728651 and 728652, respectively.
Copies of the data can be obtained free of charge on application
to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax +44(1223)336033,
e-mail: deposit@ccdc.cam.ac.uk.
