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Karapetyan V, Mkrtchyan S, Schmidt A, et al. 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. Org Biomol Chem. 2008;6(16):2961-8doi: 10.1039/b803141j.
Karapetyan, V., Mkrtchyan, S., Schmidt, A., Gütlein, J. P., Villinger, A., Reinke, H., Jiao, H., Fischer, C., & Langer, P. (2008). 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. Organic & biomolecular chemistry, 6(16), 2961-8. https://doi.org/10.1039/b803141j
Karapetyan, Vahuni, et al. "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." Organic & biomolecular chemistry vol. 6,16 (2008): 2961-8. doi: https://doi.org/10.1039/b803141j
Karapetyan V, Mkrtchyan S, Schmidt A, Gütlein JP, Villinger A, Reinke H, Jiao H, Fischer C, Langer P. 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. Org Biomol Chem. 2008 Aug 21;6(16):2961-8. doi: 10.1039/b803141j. Epub 2008 Jun 21. PMID: 18688489.
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Org Biomol Chem. 2008 Aug 21;6(16):2961-8. doi: 10.1039/b803141j. Epub 2008 Jun 21.

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.

Organic & biomolecular chemistry

Vahuni Karapetyan, Satenik Mkrtchyan, Andreas Schmidt, Jörg-Peter Gütlein, Alexander Villinger, Helmut Reinke, Haijun Jiao, Christine Fischer, Peter Langer

Affiliations

  1. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.

PMID: 18688489 DOI: 10.1039/b803141j

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.

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