European Journal of Chemistry

A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination



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Amr Mohamed Abdelmoniem
Said Ahmed Soliman Ghozlan
Holger Butenschön
Ismail Abdelshafy Abdelhamid

Abstract

Michael addition reactions of arylhydrazone derivatives with different functionalized α-cyanoacrylamides were conducted and yielded new pyridazine-4-carboxamide compounds. A further reaction with acetic anhydride was investigated resulting in the formation of a 4-deazatoxoflavin analogue. A one step synthesis of 4-deazatoxoflavin was also carried out by reacting azaenamine with N-carbamoyl-2-cyano-3-phenylacrylamide to give deazatoxoflavin. Unambiguous structural elucidation was done using 2D-HMBC spectroscopy.

 


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Abdelmoniem, A. M.; Ghozlan, S. A. S.; Butenschön, H.; Abdelhamid, I. A. A Facile Synthesis of 3-Amino-2,5-Dihydropyridazines and 4-Deazatoxoflavin Analogues via [3+3] Atom Combination. Eur. J. Chem. 2016, 7, 73-80.

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