A new type of dimroth rearrangement

Formation of 1,2-dihydro-3H-quinazolone 4-oximes from 4-amino-1,2-dihydroquinazoline 3-oxides

Dezsö Korbonits, P. Kolonits

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Contrary to earlier claims the primary product of the reaction of aldehydes and o-aminobenzamide oxime is, irrespective of the aldehyde, always a 4-amino-1,2-dihydroquinazoline 3-oxide. Thermolysis of 1-unsubstituted 2-substituted quinazoline 3-oxides (5) in solution or in melt gives rise, by a new type of Dimroth rearrangement, to the isomeric 1,2-dihydro-4-quinazolone oximes (6), while the 1-benzyl 2-unsubstituted analogue (9j) yields, presumably by an addition–elimination ring transformation coupled with oxidation, a quinoidal quinazolone 4-oxime (17).

Original languageEnglish
Pages (from-to)2163-2168
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - 1986

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Oximes
Oxides
Aldehydes
Quinazolines
Thermolysis
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "A new type of dimroth rearrangement: Formation of 1,2-dihydro-3H-quinazolone 4-oximes from 4-amino-1,2-dihydroquinazoline 3-oxides",
abstract = "Contrary to earlier claims the primary product of the reaction of aldehydes and o-aminobenzamide oxime is, irrespective of the aldehyde, always a 4-amino-1,2-dihydroquinazoline 3-oxide. Thermolysis of 1-unsubstituted 2-substituted quinazoline 3-oxides (5) in solution or in melt gives rise, by a new type of Dimroth rearrangement, to the isomeric 1,2-dihydro-4-quinazolone oximes (6), while the 1-benzyl 2-unsubstituted analogue (9j) yields, presumably by an addition–elimination ring transformation coupled with oxidation, a quinoidal quinazolone 4-oxime (17).",
author = "Dezs{\"o} Korbonits and P. Kolonits",
year = "1986",
doi = "10.1039/P19860002163",
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journal = "Journal of the Chemical Society, Perkin Transactions 1",
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T1 - A new type of dimroth rearrangement

T2 - Formation of 1,2-dihydro-3H-quinazolone 4-oximes from 4-amino-1,2-dihydroquinazoline 3-oxides

AU - Korbonits, Dezsö

AU - Kolonits, P.

PY - 1986

Y1 - 1986

N2 - Contrary to earlier claims the primary product of the reaction of aldehydes and o-aminobenzamide oxime is, irrespective of the aldehyde, always a 4-amino-1,2-dihydroquinazoline 3-oxide. Thermolysis of 1-unsubstituted 2-substituted quinazoline 3-oxides (5) in solution or in melt gives rise, by a new type of Dimroth rearrangement, to the isomeric 1,2-dihydro-4-quinazolone oximes (6), while the 1-benzyl 2-unsubstituted analogue (9j) yields, presumably by an addition–elimination ring transformation coupled with oxidation, a quinoidal quinazolone 4-oxime (17).

AB - Contrary to earlier claims the primary product of the reaction of aldehydes and o-aminobenzamide oxime is, irrespective of the aldehyde, always a 4-amino-1,2-dihydroquinazoline 3-oxide. Thermolysis of 1-unsubstituted 2-substituted quinazoline 3-oxides (5) in solution or in melt gives rise, by a new type of Dimroth rearrangement, to the isomeric 1,2-dihydro-4-quinazolone oximes (6), while the 1-benzyl 2-unsubstituted analogue (9j) yields, presumably by an addition–elimination ring transformation coupled with oxidation, a quinoidal quinazolone 4-oxime (17).

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