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Paper | Regular issue | Vol 41, No. 11, 1995, pp. 2527 - 2551
Published online:
DOI: 10.3987/COM-95-7203
Reaction Products of 1,3-Indandione with Heteroaromatic Carbaldehydes: Synthesis, Structure and NMR-Investigations

Claudia Franz, Gottfried Heinisch*, Wolfgang Holzer,* Kurt Mereiter, Barbara Strobl, and Changtu Zheng

*Institute of Pharmaceutical Chemistry, University of Vienna, Pharmaziezentrum, Althanstraße14, A-1090 Vienna, Austria

Abstract

The synthesis of 1:1 condensation products from 1,3-indandione and various heteroaromatic carbaldehydes is described. Employment of aldehydes derived from π-deficient N-heteroaromatics was found to lead also to 2:1 adducts via Michael-addition of the 1,3-diketone to the initially formed 1:1 condensation products. 1H and 13C nmr spectroscopic studies of the products obtained and of known congeners are presented. The structure of the 2:1 adduct resulting from reaction of 1,3-indandione and 4-quinolinecarbaldehyde was determined by X-ray analysis.

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