Synthesis of Azido Derivatives of Mucobromic Acid: Critical Study

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Synthesis of Azido Derivatives of Mucobromic Acid: Critical Study

July 29, 2020 Chemistry 0

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.

Author (s)  Details

N. D. Jumbam
Department of Chemistry and Chemical Technology, Faculty of Science, Engineering and Technology, Walter Sisulu University, P/Bag X1, Mthatha 5117, Eastern Cape, Republic of South Africa.

W. Masamba
Department of Chemistry and Chemical Technology, Faculty of Science, Engineering and Technology, Walter Sisulu University, P/Bag X1, Mthatha 5117, Eastern Cape, Republic of South Africa.

N. Mbebe
Department of Chemistry and Chemical Technology, Faculty of Science, Engineering and Technology, Walter Sisulu University, P/Bag X1, Mthatha 5117, Eastern Cape, Republic of South Africa.

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