3,4-Diacetylhexane-2,5-dione—an effective synthon for synthesis of substituted azulene heteroanalogs by cyclocondensation reactions View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1998-08

AUTHORS

E. P. Olekhnovich, S. L. Boroshko, Yu. N. Tkachenko, A. F. Pozharskii, E. B. Tsupak, Yu. A. Zhadanov, L. P. Olekhnovich

ABSTRACT

The one-pot method for the synthesis of 4,8-dialkoxy-6-aryl-1,3-dimethylcyclohepta [c]furanium perchlorates has been developed. The method is based on the cyclocondensation of 3,4-diacetylhexane-2,5-diones with aromatic aldehydes and trialkyl orthoformates under the action of a 16% perchloric acid solution in acetic anhydride. Under similar conditions, with hydrogen sulfide, cyclohepta[c]thiophenium perchlorates have been obtained, while cyclohepta[c]pyrrolium perchlorates have been prepared with arylamines, ammonium acetate, or aliphatic amine acetates. A heteroanalog of azulene, 4,8-diethoxy-1,3-dimethyl-2-azaazulene, has been obtained for the first time. Hydrolysis of aza- and thiaazulenium salts gives the corresponding cyclohepta[c]pyrrol-4-ones and cyclohepta [c]thiophen-4-ones. More... »

PAGES

1553-1560

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02495609

DOI

http://dx.doi.org/10.1007/bf02495609

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1046837632


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