Naphtho[2,1-h]isoquinolines: a new class of partially reduced polycyclic aromatic nucleus?

RSC Advances Pub Date: 2012-01-04 DOI: 10.1039/C2RA00767C

Abstract

An efficient de novo synthesis of partially reduced naphtho[2,1-h]isoquinolines has been developed through base catalyzed ring transformation of 2-oxo-4-sec-amino-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles by a carbanion, generated in situ from 1-substituted-4-piperidones in DMF and powdered KOH, in excellent yields. The effect of nitrogen insertion in the D ring of partially reduced benzo[c]phenanthrene on conformational changes has also been studied by X-ray diffraction analysis.

Graphical abstract: Naphtho[2,1-h]isoquinolines: a new class of partially reduced polycyclic aromatic nucleus
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