Preparation of spiropiperidines in water

Ferenc Miklós, Ferenc Fülöp

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

An environmentally benign spirocyclization is described for the synthesis of 4-spiropiperidines from 2-aminocarbohy-drazides in water at room temperature without any catalyst. The condensation of carbocyclic 2-aminocarbohydrazides with A'-benzylpiperidinone (2) led to 3'-aminospiropiperidine-quinazolinones (3a-3d). Anthranilic hydrazide 4 gave 2-amino-A''-(l-benzylpiperidin-4-ylidene) benzohydrazide (7), while glycine hydrazide (8) reacted with 2 moles of 2 to afford l-benzylpiperidin-4-ylidenamino-l,4,8-triazaspiro[4.5]decane (9). All products precipitated from the reaction mixture and were obtained in excellent yields. No further work-up or purification was necessary.

Original languageEnglish
Pages (from-to)674-679
Number of pages6
JournalActa Chimica Slovenica
Volume56
Issue number3
Publication statusPublished - Sep 30 2009

Keywords

  • Aqueous media
  • Green synthesis
  • Methylene-bridged quinazolines
  • Spirocyclization
  • Spiropiperidines
  • Spiroquinazolines

ASJC Scopus subject areas

  • Chemistry(all)

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