Simple and condensed β-lactams. Part 20. Reaction of some 1-(4-methoxyphenyl)azetidin-2-ones with cerium(IV) ammonium nitrate (CAN): Trapping of the quinone imine intermediate with chloride and iodide anions

József Fetter, Le Thanh Giang, Tibor Czuppon, Károly Lempert, Mária Kajtár-Peredy, Gábor Czira

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

1-(4-methoxyphenyl)azetidin-2-ones 12 and 13, when treated with cerium(IV) ammonium nitrate (CAN), afford either their N-deprotected derivatives (19, 26) or the chlorinated compounds 22 and 27, respectively, as the main products, depending on whether sodium chloride was present or not. A series of minor products (20, 21, 23-25 and 29, respectively) are formed in addition. 1-(4-Methoxyphenyl)azetidin-2-ones 13 and 14, when treated successively with CAN and sodium iodide, afford the corresponding 1-(4-hydroxyphenyl)azetidin-2-ones 28 and 30, respectively, in good yields. The latter reactions could possibly form the basis for elaboration of a potentially general method for dealkoxy-hydroxylation of N-(2- and 4-alkoxyphenyl)carboxamides. Mechanisms are suggested for the formation of compounds 19 - 30.

Original languageEnglish
Pages (from-to)4185-4200
Number of pages16
JournalTetrahedron
Volume50
Issue number14
DOIs
Publication statusPublished - Apr 4 1994

Keywords

  • N-Deprotection
  • Quinone Imines
  • Trapping
  • β-Lactams

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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