Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one

J. Fetter, Helga Vásárhelyi, M. Kajtár-Peredy, Károly Lempert, József Tamás, Gábor Czira

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Dephthaloylation of 3-phthalimidoazetidin-2-one 1a with methylhydrazine affords the ring transformation product 2b, rather than the expected 3-aminoazetidin-2-one 1b. Independently prepared azetidinone 1b, when treated with sodium hydroxide or methylhydrazine, is isomerized to compound 2b. A mechanism is suggested for transformation 1a → 2b. - The tautomeric structures of the majority of the potentially tautomeric compounds described were established.

Original languageEnglish
Pages (from-to)4763-4778
Number of pages16
JournalTetrahedron
Volume51
Issue number16
DOIs
Publication statusPublished - Apr 17 1995

Fingerprint

Monomethylhydrazine
Lactams
Sodium Hydroxide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one. / Fetter, J.; Vásárhelyi, Helga; Kajtár-Peredy, M.; Lempert, Károly; Tamás, József; Czira, Gábor.

In: Tetrahedron, Vol. 51, No. 16, 17.04.1995, p. 4763-4778.

Research output: Contribution to journalArticle

Fetter, J. ; Vásárhelyi, Helga ; Kajtár-Peredy, M. ; Lempert, Károly ; Tamás, József ; Czira, Gábor. / Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one. In: Tetrahedron. 1995 ; Vol. 51, No. 16. pp. 4763-4778.
@article{589b009d4a7147efba040a8758191c65,
title = "Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one",
abstract = "Dephthaloylation of 3-phthalimidoazetidin-2-one 1a with methylhydrazine affords the ring transformation product 2b, rather than the expected 3-aminoazetidin-2-one 1b. Independently prepared azetidinone 1b, when treated with sodium hydroxide or methylhydrazine, is isomerized to compound 2b. A mechanism is suggested for transformation 1a → 2b. - The tautomeric structures of the majority of the potentially tautomeric compounds described were established.",
author = "J. Fetter and Helga V{\'a}s{\'a}rhelyi and M. Kajt{\'a}r-Peredy and K{\'a}roly Lempert and J{\'o}zsef Tam{\'a}s and G{\'a}bor Czira",
year = "1995",
month = "4",
day = "17",
doi = "10.1016/0040-4020(95)00158-5",
language = "English",
volume = "51",
pages = "4763--4778",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "16",

}

TY - JOUR

T1 - Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one

AU - Fetter, J.

AU - Vásárhelyi, Helga

AU - Kajtár-Peredy, M.

AU - Lempert, Károly

AU - Tamás, József

AU - Czira, Gábor

PY - 1995/4/17

Y1 - 1995/4/17

N2 - Dephthaloylation of 3-phthalimidoazetidin-2-one 1a with methylhydrazine affords the ring transformation product 2b, rather than the expected 3-aminoazetidin-2-one 1b. Independently prepared azetidinone 1b, when treated with sodium hydroxide or methylhydrazine, is isomerized to compound 2b. A mechanism is suggested for transformation 1a → 2b. - The tautomeric structures of the majority of the potentially tautomeric compounds described were established.

AB - Dephthaloylation of 3-phthalimidoazetidin-2-one 1a with methylhydrazine affords the ring transformation product 2b, rather than the expected 3-aminoazetidin-2-one 1b. Independently prepared azetidinone 1b, when treated with sodium hydroxide or methylhydrazine, is isomerized to compound 2b. A mechanism is suggested for transformation 1a → 2b. - The tautomeric structures of the majority of the potentially tautomeric compounds described were established.

UR - http://www.scopus.com/inward/record.url?scp=0028936046&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028936046&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(95)00158-5

DO - 10.1016/0040-4020(95)00158-5

M3 - Article

AN - SCOPUS:0028936046

VL - 51

SP - 4763

EP - 4778

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 16

ER -