Unusual synthesis of azines and their oxidative degradation to carboxylic acid using iodobenzene diacetate

ABSTRACT

Reaction of 3-hydrazonobutan-2-one oxime with aromatic aldehydes resulted in the formation of 1,2-bis(arylidene)hydrazine commonly referred as azine as an unexpected product, instead of expected product 3-(aryl)methylenehydrazonobutan-2-one oxime, which were subsequently oxidized to corresponding aromatic acids with an ecofriendly oxidizing agent iodobenzene diacetate. Azines and carboxylic acids were characterized by IR and NMR (¹H, ¹³C, HMBC, and HMQC) studies.

GRAPHICAL ABSTRACT

KEYWORDS:

• 3-Hydrazonobutan-2-one oxime
• aromatic acid
• azine
• iodobenzene diacetate
• oxidative degradation

Additional information

Funding

We are thankful to Council of Scientific and Industrial Research (CSIR), New Delhi, India for providing Junior Research Fellowship (Grant 09/105(0236/2016-EMR-1).