Simple and condensed β-lactams. Part 14. anomalous behaviour of 1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one towards cerium(IV) ammonium nitrate

J. Fetter, Ernö Keskeny, Tibor Czuppon, Károly Lempert, M. Kajtár-Peredy, József Tamás

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Abstract

Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I).

Original languageEnglish
Pages (from-to)3061-3067
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number22
DOIs
Publication statusPublished - 1992

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Lactams
Imines
Deprotonation
Reducing Agents
Sodium Chloride
Hydrolysis
Derivatives
benzoquinone
cerium(IV) ammonium nitrate

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Simple and condensed β-lactams. Part 14. anomalous behaviour of 1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one towards cerium(IV) ammonium nitrate",
abstract = "Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I−).",
author = "J. Fetter and Ern{\"o} Keskeny and Tibor Czuppon and K{\'a}roly Lempert and M. Kajt{\'a}r-Peredy and J{\'o}zsef Tam{\'a}s",
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T1 - Simple and condensed β-lactams. Part 14. anomalous behaviour of 1-(4-methoxyphenyl)-4-(tetrazol-5-ylmethyl)azetidin-2-one towards cerium(IV) ammonium nitrate

AU - Fetter, J.

AU - Keskeny, Ernö

AU - Czuppon, Tibor

AU - Lempert, Károly

AU - Kajtár-Peredy, M.

AU - Tamás, József

PY - 1992

Y1 - 1992

N2 - Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I−).

AB - Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I−).

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