ZnCl2-Promoted Intramolecular Hetero Diels–Alder Reaction of o-Alkynylphenylcarbodiimides for Synthesis of Dihydrodibenzo[b,g][1,8]naphthyridines

Noriki Kutsumura; Yasuaki Koyama; Kotaro Tateno; Naoshi Yamamoto; Hiroshi Nagase; Takao Saito

doi:10.1248/cpb.c16-00363

This article has now been updated. Please use the final version.

ZnCl₂-Promoted Intramolecular Hetero Diels–Alder Reaction of o-Alkynylphenylcarbodiimides for Synthesis of Dihydrodibenzo[b,g][1,8]naphthyridines

Noriki Kutsumura , Yasuaki Koyama, Kotaro Tateno, Naoshi Yamamoto, Hiroshi Nagase, Takao Saito

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Keywords: Hetero-Diels–Alder, carbodiimide, naphthyridine, zinc chloride, heterocycle, one-pot

JOURNAL FREE ACCESS Advance online publication

Article ID: c16-00363

DOI https://doi.org/10.1248/cpb.c16-00363

The final version of this article is now available: Vol. 64 (2016), No. 9 pp. 1364-1369

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Abstract

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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