Issue 16, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines†

Vahuni Karapetyan,a   Satenik Mkrtchyan,a   Andreas Schmidt,a   Jörg-Peter Gütlein,a   Alexander Villinger,a   Helmut Reinke,a   Haijun Jiao,b   Christine Fischerb  and  Peter Langer*ab  

* Corresponding authors

a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
E-mail: peter.langer@uni-rostock.de
Fax: 00 49 381 49864112
Tel: 0049 381 4986410

b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Abstract

A variety of functionalized 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes were prepared by one-pot cyclizations of 1,3-bis(silyl enol ethers) with quinazolines. The mechanism of the cyclization was studied by B3LYP/6-31G(d) density functional theory computations. The products could be functionalized by Suzuki cross-coupling reactions. The reaction of 1,3-bis(silyl enol ethers) with phthalazine afforded open-chain rather than cyclization products.

Graphical abstract: Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines

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Article information

DOI
https://doi.org/10.1039/B803141J
Article type
Paper
Submitted
22 Feb 2008
Accepted
16 May 2008
First published
21 Jun 2008

Org. Biomol. Chem., 2008,6, 2961-2968

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Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines

V. Karapetyan, S. Mkrtchyan, A. Schmidt, J. Gütlein, A. Villinger, H. Reinke, H. Jiao, C. Fischer and P. Langer, Org. Biomol. Chem., 2008, 6, 2961 DOI: 10.1039/B803141J

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