Synthesis of aminomethylazetidines regioselective reactions of mesyloxymethylazetidinones with nucleophiles II

Éva Boros, Ferenc Bertha, Gàbor Czira, Antal Feller, J. Fetter, M. Kajtár-Peredy, Gyula Simig

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Two efficient methods have been developed for the synthesis of variously substituted 2-aminomethylazetidine derivatives 5 by regioselective nucleophilic substitution of 4-mesyloxymethylazetidin-2-ones 3 followed by reduction or by reduction of the appropriate 4-oxo-azetidine-2-carboxamides 7. A novel ring transformation of 4-oxoazetidine-2-carboxamides 7 into tetrahydroquinolines 16 by reaction with lithium aluminium hydride / aluminium trichloride has been investigated.

Original languageEnglish
Pages (from-to)371-388
Number of pages18
JournalJournal of Heterocyclic Chemistry
Volume43
Issue number2
DOIs
Publication statusPublished - Mar 2006

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Nucleophiles
Substitution reactions
Derivatives
S-2-aminomethylazetidine
1,2,3,4-tetrahydroquinoline
azetidine
lithium aluminum hydride
aluminum chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of aminomethylazetidines regioselective reactions of mesyloxymethylazetidinones with nucleophiles II. / Boros, Éva; Bertha, Ferenc; Czira, Gàbor; Feller, Antal; Fetter, J.; Kajtár-Peredy, M.; Simig, Gyula.

In: Journal of Heterocyclic Chemistry, Vol. 43, No. 2, 03.2006, p. 371-388.

Research output: Contribution to journalArticle

Boros, Éva ; Bertha, Ferenc ; Czira, Gàbor ; Feller, Antal ; Fetter, J. ; Kajtár-Peredy, M. ; Simig, Gyula. / Synthesis of aminomethylazetidines regioselective reactions of mesyloxymethylazetidinones with nucleophiles II. In: Journal of Heterocyclic Chemistry. 2006 ; Vol. 43, No. 2. pp. 371-388.
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