Intramolecular [2+2+2] cycloaddition of bis(propargylphenyl)carbodiimides: synthesis of L-shaped π-extended compounds with pyrrolo[1,2-a][1,8]naphthyridine corner units

Takashi Otani; Takao Saito; Ryota Sakamoto; Hiroyuki Osada; Akihito Hirahara; Naoki Furukawa; Noriki Kutsumura; Tsukasa Matsuo; Kohei Tamao

doi:10.1039/c3cc42792g

Intramolecular [2+2+2] cycloaddition of bis(propargylphenyl)carbodiimides: synthesis of L-shaped π-extended compounds with pyrrolo[1,2-a][1,8]naphthyridine corner units

Chem Commun (Camb). 2013 Jul 14;49(55):6206-8. doi: 10.1039/c3cc42792g.

Authors

Takashi Otani¹, Takao Saito, Ryota Sakamoto, Hiroyuki Osada, Akihito Hirahara, Naoki Furukawa, Noriki Kutsumura, Tsukasa Matsuo, Kohei Tamao

Affiliation

¹ Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Tokyo 162-8601, Japan.

PMID: 23736526
DOI: 10.1039/c3cc42792g

Abstract

L-shaped π-extended penta-, hexa-, and heptacycles with a pyrrolo[1,2-a][1,8]naphthyridine junction were prepared from N,N'-bis[2-(2-alkyn-1-yl)phenyl]carbodiimides or their naphthyl analogs via Rh(I)-catalyzed intramolecular [2+2+2] cycloaddition and dehydrogenative aromatization. These L-shaped compounds emit sky-blue, yellow-green, or golden-orange fluorescence, with high quantum yields.