ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of new quinoxalinophenazinediones and tetrahydrobenzodipyrrolotetrones of biological interest

Ahmed S. Hammam, Mohamed S. K. Youssef, Ferial M. Atta, and Thana A. Mohamed

Department of Chemistry, Faculty of Science, Assiut University, 71516 Assiut, Egypt

E-mail: salah_kamel2000@yahoo.com

Received: 10 March 2007  Revised: 1 July 2007  Accepted: 19 July 2007

Abstract: The reaction of two equivalents of sodium azide with diarylaminodibromo-p-benzoquinone (I) in DMF for 15–24 h produced quinoxalinophenazinediones together with a byproduct identified as diarylaminodiaminobenzoquinone. On the other hand, the reaction of bromanil with active methylenes, such as diethyl malonate and ethyl acetoacetate, resulted in disubstitution products which, on treatment with primary amines, cyclized into benzodipyrroletetrones. Comparative antifungal and antibacterial studies were made.

Keywords: quinoxalinophenazinediones - tetrahydrobenzodipyrrolotetrones - synthesis - antimicrobial activity - antifungal activity - acute toxicity

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-008-0011-5

Chemical Papers 62 (2) 194–206 (2008)