Ac oncise and efficient synthesis of acenaphtho [1,2-b]indoles with different substitution patternsf rom a[ 3+ +2] condensation of enaminones with acenaphthoquinone has been developed. During the first pathway,p roducts 3 were synthesized in the presence of Et 3 N, while as econd reactioni nt he presence of p-toluenesulfonic acid leads to compounds 5 via intramolecular cyclization and highly regioselectiveS N 1-typer eactionw ith alcoholsu nder solvent-free conditions. Both procedures give excellent yields and are highly eco-benign, are convenient one-pot operations, are highly regioselectivity,a nd use environmentally friendly solvent systems or operate under solvent-free conditions. This method offers an alternative to regioselective construction of biologically meaningful polycyclic indoles.
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