Synthesis of azido derivatives of mucobromic acid

• Main Authors: N. Mbebe, W. Masamba, N. D. Jumbam
• Format: Article
• Language: English
• Published: Chemical Society of Ethiopia 2013-04-01
• Series: Bulletin of the Chemical Society of Ethiopia
• Subjects: 3; 4-Diazido-5-hydroxyfuran-2(5H)-one; 4-diazido-5-methoxyfuran-2(5H)-one; 4; 5-Diazidopyridazinones; Mucobromic acid
• Online Access: http://www.ajol.info/index.php/bcse/article/view/84087

Mucobromic acid is a highly reactive multicentered molecule. It was converted to its corresponding but unstable diazido derivative by reaction with two equivalents of sodium azide. The resultant 3,4-diazido-5-hydroxyfuran-2(5H)-one was obtained in moderate yield (42%) but decomposed readily even at low temperatures. Its more stable analogue 3,4-diazido-5-methoxyfuran-2(5H)-one was obtained in excellent yield after reacting 5-methoxy-3,4-dibromofuranone with two equivalents of sodium azide. The 4,5-dibromopyridazinones which are in effect masked mucobromic acid derivatives, underwent nucleophilic substitution reactions with various nucleophiles, including azides and afforded corresponding azidopyridazinones in good yields. The synthesized azido-furanone and pyridazinone derivatives are earmarked for click reactions.DOI: http://dx.doi.org/10.4314/bcse.v27i1.17