tailieunhanh - Utility of 4-formylantipyrine in heterocyclic synthesis
Pyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione, pyrano[2,3-c]pyrazole-5-carbonitrile, pyrano[2,3-d]4-imidazolines, pyrido[2,1-b]benzimidazole, pyrido[2,1-b][1,3]benzoxazole, pyrido[2,1- b][1,3]benzothiazole and pyrido[2,1-b]quinazoline were synthesised from antipyrine derivatives with appropriate reagents such as maleimides, malononitrile, ethyl cyanoacetate, benzimidazole-2-acetonitrile, benzothiazole-2-acetonitrile, benzoxazol-2-acetonitrile, benzoylacetonitrile and other reagents. The newly synthesised compounds were established by elemental analysis, spectral data, and alternative synthetic routes whenever possible. | Journal of Advanced Research 2010 1 137-144 Cairo University Journal of Advanced Research ORIGINAL ARTICLE Utility of 4-formylantipyrine in heterocyclic synthesis Abdou O. Abdelhamid Mamdouh . Afifi Department of Chemistry Faculty of Science Cairo University Giza 12613 Egypt Available online 6 March 2010 KEYWORDS Pyrrolo 3 4-c pyrazole Pyrano 2 3-c pyrazole Pyrido 2 1- benzimidazole Pyrido 2 1- 1 3 benzoxazole Pyrido 2 1- 1 3 benzothiazole Pyrido 2 1- quinazoline Abstract Pyrrolo 3 4-c pyrazole-4 6 1H 5H -dione pyrano 2 3-c pyrazole-5-carbonitrile pyrano 2 3-d 4-imidazolines pyrido 2 1- benzimidazole pyrido 2 1- 1 3 benzoxazole pyrido 2 1- 1 3 benzothiazole and pyrido 2 1- quinazoline were synthesised from antipyrine derivatives with appropriate reagents such as maleimides malononitrile ethyl cyanoacetate benzimidazole-2-acetonitrile benzothiazole-2-acetonitrile benzoxazol-2-acetonitrile benzoylacetonitrile and other reagents. The newly synthesised compounds were established by elemental analysis spectral data and alternative synthetic routes whenever possible. 2010 Cairo University. All rights reserved. Introduction Antipyrine derivatives have attracted the attention of several research groups due their potential activities 1-5 . In this a broad spectrum of bioactive antipyrine derivatives have been investigated and diversities of bioactivities such as analgesic 6 7 anti-inflammatory 8 antimicrobial 9-11 and anticancer activity 12 have been reported. In continuation of our research 13-18 we report herein the synthesis of some new heterocycles incorporating the antipyrine moiety starting from 4-formylantipyrine. Experimental All melting points were determined on an electrothermal apparatus and are reported here uncorrected. IR spectra were recorded KBr discs on a Shimadzu FT-IR 8201 PC spectrophotometer. 1H Corresponding author. Tel. 202 37489611 fax 202 35727556. E-mail address Abdelhamid45@ . Abdelhamid . 2090-1232 2010 Cairo University. Production
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