Anionic Cascade Routes to Sulfur and Nitrogen Heterocycles Originating from Thio- and Aminophosphate Precursors

Pradipta Das, Jon T. Njardarson

Research output: Contribution to journalReview articlepeer-review

5 Scopus citations

Abstract

This micro-review attempts to comprehensively cover reported reactions employing thio- and aminophosphate precursors for forming sulfur and nitrogen heterocycles. All such reactions are triggered by initial formation of an alkoxide, most commonly by attack of a carbon or heteroatom nucleophile onto a carbonyl group. The alkoxide intermediate facilitates an intramolecular transfer of the phosphate group to form a thiolate or nitrogen atom anion, which then terminate the anionic cascade via an intramolecular O-phosphate displacement reaction to form the heterocyclic products.

Original languageEnglish (US)
Pages (from-to)4249-4259
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number25
DOIs
StatePublished - Sep 2016

Keywords

  • Aminophosphates
  • Cascade reactions
  • Nitrogen heterocycles
  • Sulfur heterocycles
  • Thiophosphates

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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