The ZnCl2-promoted intramolecular hetero-Diels-Alder reaction of N-(ortho-propargylphenyl)-N'-arylcarbodiimides, in which the aryl-N=C moiety functioned as a 2-azabuta-1,3-diene, 4π component, has been achieved. By this method, very rare 5,12-dihydrodibenzo[b,g][1,8]naphthyridines and fully aromatized dibenzo[b,g][1,8]naphthyridines were successfully synthesized.
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http://dx.doi.org/10.1248/cpb.c16-00363 | DOI Listing |
Chem Pharm Bull (Tokyo)
September 2016
International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba.
The ZnCl2-promoted intramolecular hetero-Diels-Alder reaction of N-(ortho-propargylphenyl)-N'-arylcarbodiimides, in which the aryl-N=C moiety functioned as a 2-azabuta-1,3-diene, 4π component, has been achieved. By this method, very rare 5,12-dihydrodibenzo[b,g][1,8]naphthyridines and fully aromatized dibenzo[b,g][1,8]naphthyridines were successfully synthesized.
View Article and Find Full Text PDFOrg Lett
January 2014
State Key Laboratory of Supramolecular Structure and Materials, School of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, People's Republic of China.
A concise and efficient method for the synthesis of a wide range of acridine derivatives and polycyclic aza-aromatic compounds from a ZnCl2-promoted cyclization reaction of readily available o-arylaminophenyl Schiff base compounds under convenient conditions was developed. Reaction conditions and scope of the new method were examined in detail.
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