Microwave-assisted synthesis of highly functionalized guanidines on soluble polymer support

Chih Hau Chen, Chieh Li Tung, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

An efficient method for the N,N′-di(Boc)-protected guanidines containing piperazine and homopiperazine scaffolds has been developed under multi-step microwave irradiation. Followed by alkylation of carbamate-protected guanidines with various alkyl halides is also explored. This protocol proceeds via deprotonation of the acidic N-carbamate hydrogen of the guanidine by sodium hydride on soluble polymer support. In this manner, highly functionalized guanidines were obtained after cleavage from the support. The reaction is tolerant of a wide range of functional groups on both the alkyl halide and guanidine components. In addition, the reaction is sufficiently simple workup by precipitation in each step to yield the substituted guanidines in high purity. In conjunction with microwave irradiation and soluble polymer support, this method provides an efficient route to access highly functionalized guanidines.

Original languageEnglish
Pages (from-to)3959-3962
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number31
DOIs
StatePublished - 1 Aug 2012

Keywords

  • Carbamate-protected guanidines
  • Microwave irradiation
  • Soluble polymer support

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