A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)

Youhei Takeda; Masato Okazaki; Yoshiaki Maruoka; Satoshi Minakata

doi:10.3762/bjoc.11.2

Beilstein Journal of Organic Chemistry (Jan 2015)

A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)

Youhei Takeda,
Masato Okazaki,
Yoshiaki Maruoka,
Satoshi Minakata

Affiliations

Youhei Takeda: Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
Masato Okazaki: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
Yoshiaki Maruoka: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan
Satoshi Minakata: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan

DOI: https://doi.org/10.3762/bjoc.11.2
Journal volume & issue: Vol. 11, no. 1
pp. 9 – 15

Abstract

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A facile and moderately functional-group-tolerant synthetic method for the preparation of 7,8-diaza[5]helicenes has been developed. It comprises of an oxidative ring-closing process of 1,1’-binaphthalene-2,2’-diamine (BINAM) derivatives with a chlorine-containing oxidant (t-BuOCl) in the presence of a base (2,6-lutidine). In addition the basic physicochemical properties of newly synthesized compounds have been investigated.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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