Efficient One-Step Synthesis of C₃-Symmetrical Benzenoid Compounds Mediated by SOCl₂/EtOH

Abstract

An efficient one-step synthesis of branched functionalized benzenoid compounds from aryl methyl ketones mediated by SOCl₂/EtOH is described; some novel C ₃-symmetrical molecules were prepared with satisfactory yields. The method enjoys short reaction time and simple operation, and avoids use of organometallic reagents.

GRAPHICAL ABSTRACT

Keywords:

• Aryl methyl ketone
• carbazole
• C ₃-symmetrical molecules
• cyclotrimerization
• thionyl chloride

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the Higher School Science and Technology Development Project of Shanxi Province Education Department (No. 2010124), the Higher School Students Science and Technology Innovation Project of Shanxi Province ([2011]11, No. 2011332), and the Project of Xinzhou Teachers University ([2011]52).

Notes

^a The reaction was run with acetophenone (0.075 mol), 25 mL CH₂Cl₂, and 9.1 mL SOCl₂ (0.125 mol).

^a The reactions were run with aryl methyl ketone (0.075 mol), 22 mL absolute ethanol, and 9.1 mL SOCl₂ (0.125 mol).

^b The reaction was monitored by thin-layer chromatography (TLC).

^c Isolated yields.