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Issue 55, 2013
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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,ab   Takao Saito,*a   Ryota Sakamoto,a   Hiroyuki Osada,a   Akihito Hirahara,a   Naoki Furukawa,a   Noriki Kutsumura,a   Tsukasa Matsuob  and  Kohei Tamaob  
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* Corresponding authors

a Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
E-mail: tsaito@rs.kagu.tus.ac.jp
Fax: +81 (0)3-5261-4631

b Functional Elemento-Organic Chemistry Unit, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

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.

Graphical abstract: 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

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Article information

https://doi.org/10.1039/C3CC42792G
Submitted
16 Apr 2013
Accepted
22 May 2013
First published
23 May 2013
Chem. Commun., 2013,49, 6206-6208
Article type
Communication
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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

T. Otani, T. Saito, R. Sakamoto, H. Osada, A. Hirahara, N. Furukawa, N. Kutsumura, T. Matsuo and K. Tamao, Chem. Commun., 2013, 49, 6206
DOI: 10.1039/C3CC42792G

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