Issue 23, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

New access to 1,3-dialkyl-2,3-dihydro-2-imino-1H-imidazoles and their application to the first total synthesis of naamine B, a marine 2,3-dihydro-2-imino-1,3-dimethyl-1H-imidazole alkaloid

Ikuo Kawasaki,a   Seikou Nakamura,a   Satomi Yanagitani,a   Akiko Kakuno,a   Masayuki Yamashitaa  and  Shunsaku Ohta*a  

* Corresponding authors

a Kyoto Pharmaceutical University, Misasagi Yamashinaku, Kyoto 607-8414, Japan
E-mail: sohta@mb.kyoto-phu.ac.jp

Abstract

1,3-Dialkyl-2,3-dihydro-2-imino-1H-imidazole derivatives are synthesized in 49–86% yield by treatment of 1,3-dialkyl-2-(phenylsulfanyl)imidazolium salts with primary carbamates or amides in the presence of a base such as LDA or NaH, and the first total synthesis of naamine B, a marine 2-imino-2,3-dimethyl-1,3-dihydro-1H-imidazole alkaloid, is achieved by application of this reaction as a key step.

Graphical abstract: New access to 1,3-dialkyl-2,3-dihydro-2-imino-1H-imidazoles and their application to the first total synthesis of naamine B, a marine 2,3-dihydro-2-imino-1,3-dimethyl-1H-imidazole alkaloid

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Article information

DOI
https://doi.org/10.1039/B108762B
Article type
Paper
Submitted
27 Sep 2001
Accepted
22 Oct 2001
First published
14 Nov 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 3095-3099

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New access to 1,3-dialkyl-2,3-dihydro-2-imino-1H-imidazoles and their application to the first total synthesis of naamine B, a marine 2,3-dihydro-2-imino-1,3-dimethyl-1H-imidazole alkaloid

I. Kawasaki, S. Nakamura, S. Yanagitani, A. Kakuno, M. Yamashita and S. Ohta, J. Chem. Soc., Perkin Trans. 1, 2001, 3095 DOI: 10.1039/B108762B

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