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

Regular Articles

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

Author information

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

JOURNAL FREE ACCESS FULL-TEXT HTML

2016 Volume 64 Issue 9 Pages 1364-1369

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

Browse “Advance online publication” version

Details

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.

Graphical Abstract Fullsize Image

Corresponding author

Register with J-STAGE for free!