Oxidative cyclization by lead(IV) acetate of 1-(4-methoxyphenyl)-4- (tetrazol-5-ylmethyl)azetidin-2-ones to 3-methoxy-9,9a-dihydroazeto[1,2- a]tetrazolo[5,1-ad][1,5]benzodiazepin-11 (10H)-ones and related reactions

Giang Le Thanh, József Fetter, Mária Kajtár-Peredy, Károly Lempert, Ferenc Bertha, György M. Keseru, Gábor Czira, Tibor Czuppon

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Abstract

The tetrazolyl groups of azetidin-2-ones 1a-e and 1h interfere with the normal reaction of related azetidin-2-ones with lead(IV) acetate, viz. acetoxylation at C-4, and cause formation of tetracyclic products 3a-e and 3h. Similar reactions take place with ring homologues 1f, 1g and 1i, and with open-chain analogues 11a and 11b.

Original languageEnglish
Pages (from-to)8457-8474
Number of pages18
JournalTetrahedron
Volume55
Issue number28
DOIs
Publication statusPublished - Jul 9 1999

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Keywords

  • Azetidinones
  • Condensed diazepines
  • Oxidative aromatic nucleophilic substitution
  • Tetrazoles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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