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Paper | Regular issue | Vol 71, No. 3, 2007, pp.619-626
Published online, 26th January, 2007
DOI: 10.3987/COM-06-10971
A New One-Step Synthesis of 1,2,4-Triazino[2,3-c]quinazolines

Oleksandr V. Karpenko,* Sergiy I. Kovalenko, Oleksiy O. Chekotylo, and Svitlana V. Shishkina

*Department of Pharmaceutical Chemistry, Zaporizhzhia State Medical University, prosp. Mayakovskogo 26, Zaporizhzhia, 69035, Ukraine

Abstract

A new and efficient one-step protocol for the synthesis of 3-substituted 2H-1,2,4-triazino[2,3-c]quinazolin-2-ones (5) was developed starting from 4-hydrazinoquinazoline (1) and α-ketocarboxylic acids and their esters. Corresponding hydrazones (2a,c and 3a,c,e) were isolated as intermediate products. Further cyclocondensation followed by acid-catalyzed Dimroth rearrangement resulted in the title derivatives 5.