Issue 7, 1988
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Formation of oxygen-bridged heterocycles in the hantzsch synthesis with 4-(2-hydroxyphenyl)but-3-en-2-one

Jan Světlík,   František Tureček  and  Vladimír Hanuš  

Abstract

Condensations of 4-(2-hydroxyphenyl)but-3-2-one with methyl acetoacetate, pentane-2,4-dione, dimedone, and methyl cyanoacetate under the conditions of the Hantzsch synthesis lead to 9-methyl-8-oxa-10-azatricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraene derivatives and related heterocycles. An analogous condensation with 2-aminopropene-1,1,3-triscarbonitrile yields stereoselectively 11-dicyanomethylene-9-methyl-8-oxa-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-triene-12α-carbonitrile. Under suitable reaction conditions, the condensation of 4-(2-hydroxyphenyl)but-3-en-2-one with cyanamide affords various products with the 9-methyl-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraene skeleton. Condensation products of salicylaldehyde with acetone, 2-aminopropene-1,1,3-triscarbonitrile, and 3-aminocrotononitrile have been identified.

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/P19880002053
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 2053-2058

Permissions

Request permissions

Formation of oxygen-bridged heterocycles in the hantzsch synthesis with 4-(2-hydroxyphenyl)but-3-en-2-one

J. Světlík, F. Tureček and V. Hanuš, J. Chem. Soc., Perkin Trans. 1, 1988, 2053 DOI: 10.1039/P19880002053

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements