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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Online
ISSN
1865-7117
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Volume 34, Issue 3 (Mar 1979)

Issues

Synthesis of 2-Cinnamoyl-1,3-indandione Derivatives and their Reactions with Hydrazine, Hydroxylamine Hydrochloride, Thiourea, Secondary Amines and Diethyl Oxalate

El - Sayed Afsah
  • Chemistry Department, Faculty of Science, Mansoura University, Mansoura, A. R. Egypt
/ Fathy Abdel Kader Amer
  • Chemistry Department, Faculty of Science, Mansoura University, Mansoura, A. R. Egypt
/ Hassan Etman
  • Chemistry Department, Faculty of Science, Mansoura University, Mansoura, A. R. Egypt
Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-1979-0326

Abstract

A series of 2-cinnamoyl-1,3-indandiones (2a-e) were obtained by condensing 1 with aldehydes. Treatment of 2 a with hydrazine or hydroxylamine hydrochloride gave 2-(5-phenyl-2-pyrazolinyl or -isoxazolinyl)-1,3-indandione (3 and 5) respectively, and when treated with thiourea gave 2-(6-phenyl-2-thioxo-4-pyrimidinyl)-1,3-indandione (6).

The formation of 2-(β-piperidino-, -morpholino- and -arylmercaptohydrocinnamoyl)- 1,3-indandiones (7a-b and 8a-b) from 2 a was investigated. Compound 7b when treated with hydrazine gave 9. The 2-(α, β-dimorpholinohydrocinnamoyl) derivative (11) was obtained by the action of morpholine on the dibromo derivative (10). The Michael condensation of 2a with ethyl acetoacetate or acetyl acetone was investigated. Treatment of 1 with benzaldehyde in (3:1) molar ratio gave 14, which reacted with diethyl oxalate to give 15. Cyclization of 15 with polyphosphoric acid lead to the formation of 16.

Keywords: 2-Cinnamoyl-1,3-indandione Derivatives

About the article

Received: 1978-10-25

Published Online: 2014-06-02

Published in Print: 1979-03-01


Citation Information: Zeitschrift für Naturforschung B, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-1979-0326. Export Citation

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. (CC BY-NC-ND 3.0)

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