Guanidine hydrochloride catalyzed efficient one-pot pseudo five-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) in water

Abstract

The present methodology describes an efficient, environmentally friendly and simple protocol for the synthesis of some 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives through a one-pot pseudo-five-component reaction of hydrazine hydrate/phenyl hydrazine, ethyl acetoacetate, and various aromatic aldehydes catalyzed by guanidine hydrochloride. This condensation reaction was performed by tandem Knoevenagel–Michael reaction in water under refluxing conditions giving the title compounds in 82–92% yields. Atom economy, simple operation, easy work-up, using inexpensive organocatalyst, high yields in short times, clean transformation, and environmentally benign are some of the important features of this new protocol.

GRAPHICAL ABSTRACT

KEYWORDS:

• 4,4′-(Arylmethylene)bis(1H-pyrazol-5-ols)
• guanidine hydrochloride
• Knoevenagel–Michael
• water

Additional information

Funding

The authors thank the Research Council of Payame Noor University and Islamic Azad University, Qaemshahr Branch for financial support.