An Efficient Method for the Synthesis of 2',3'-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

Chem Pharm Bull (Tokyo). 2016;64(12):1763-1768. doi: 10.1248/cpb.c16-00625.

Abstract

An efficient and practical synthesis of 2',3'-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.

MeSH terms

  • Molecular Structure
  • Onium Compounds / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Sulfonium Compounds / chemistry*

Substances

  • Onium Compounds
  • Spiro Compounds
  • Sulfonium Compounds