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1,3-Dipolar cycloaddition of diazoalkanes onto dimethyl 1-(formylamino)ethylenephosphonate: a new route to 1-aminocyclopropanephosphonic acids and 3-phosphorylated pyrazoles

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
67
Issue
49
Identifiers
DOI: 10.1016/j.tet.2011.10.010
Keywords
  • 1
  • 3-Dipolar Cycloaddition
  • 1-Aminocyclopropanephosphonates
  • Phosphorylated Pyrazoles

Abstract

Abstract Diazoalkanes regiospecifically react with dimethyl 1-(formylamino)ethylenephosphonate ( 1a) to afford 5-substituted dimethyl 3-(formylamino)-4,5-dihydro-3 H-pyrazol-3-phosphonates 2 in high yields. Their thermal decomposition followed by hydrolysis provides a straightforward access to 2-substituted 1-aminocyclopropanephosphonic acids 4. Aromatization of 2 under acidic conditions leads to 3-phosphorylated pyrazoles 5.

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