Preparation, characterization and testing the catalytic activity of a new acidic ionic liquid in multicomponent reactions

Authors

• Abdolkarim Zare ¹
• Elaheh Sharif ²
• Azam Arghoon ²
• Marzieh Ghasemi ²
• Bentolhoda Dehghani ²
• Sorayya Ahmad-Zadeh ²
• Fatemeh Zarei ²

1. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran
2. Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran.

Abstract

In this study, N¹,N¹,N²,N²-tetramethylethane-1,2-diamine was reacted with chlorosulfonic acid to afford N¹,N¹,N²,N²-tetramethyl-N¹,N²-bis(sulfo)ethane-1,2-diaminium chloride ([TMBSED][Cl]₂) as a new acidic ionic liquid. [TMBSED][Cl]₂ was identified by ¹H and ¹³C NMR, mass and FT-IR spectra. Then, its catalytic activity was examined to promote the following multicomponent reactions: (i) the production of 4,4´-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s from arylaldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one in ethanol, and (ii) the synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones from arylaldehydes, dimedone and 2-naphthol in solvent-free conditions. The ionic liquid was highly efficient and general catalyst for these reactions.

Keywords

• 12-Aryl-8
• Acidic ionic liquid
• [TMBSED][Cl]2
• 4´-(Arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
• 12-tetrahydrobenzo[a]xanthen-11-one