Synthesis of 5,6-dihydrobenz[c]acridines: a comparative study

Add time:07/17/2019    Source:sciencedirect.com

5,6-Dihydrobenz[c]acridines were synthesized by the reaction of 1-chloro-3,4-dihydro-2-naphthaldehyde with aromatic amines under three different conditions:a.Thermolysis of 1-chlorovinyl-(N-aryl)imines prepared from 1-chloro-3,4-dihydro-2-naphthaldehyde.b.Acid catalyzed cyclization of 1-(N-aryl)amino-3,4-dihydro-2-naphthaldehydes.c.Thermolysis of N-arylenaminoimine hydrochlorides derived from 1-chloro-3,4-dihydro-2-naphthaldehyde in DMF medium.All the three approaches exclusively yielded only 5,6-dihydrobenz[c]acridines and not the isomeric 7,8-dihydrobenzo[k]phenanthridines.The structures of these products have been unambiguously established by detailed NMR spectral study and by independent synthesis as well as by single crystal XRD study.

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