Syntheses of indolyl-4(3H)-quinazolinones

I. Hermecz, J. Kökösi, Benjamin Podányi, G. Szász

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Abstract

2-(1H-Indol-2-yl)-4(3H)-quinazolinones (10, 11) and 2-(2-ethoxy-carbonyl-1H-indol-3-yl)-4(3H)-quinazolin-4-one (15) are prepared by the Fischer indolization of 2-(1-phenylhydrazonoalkyl)- (8, 9) and 2-(2-phenylhydrazono-2-ethoxycarbonylethyl)-4(3H)-quinazolinones (14), respectively, by heating in PPA. When 2-phenylhydrazone derivative (14) is heated in 85% phosphoric acid at 180 °C, besides indolization ester hydrolysis and decarboxylation also occurred to yield 2-(1H-indol-3-yl)-4(3H)-quinazolinone (16). The 3-(1H-indol-3-yl)-4(3H)-quinazolinone (24) is prepared either from the isomeric 3-indolyl derivatives of anthranilamide (21, 23) by heating in 98% formic acid, or in "one pot" procedure from 2-[1-(N-methyl-N-phenylamino)ethyl]-4(3H)-quinazolinone (17) by heating in 98% formic acid in the presence of a few drops of conc. hydrochloric acid. The reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)903-914
Number of pages12
JournalHeterocycles
Volume37
Issue number2
Publication statusPublished - Mar 3 1994

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formic acid
Heating
Derivatives
Decarboxylation
Hydrochloric Acid
4-hydroxyquinazoline
Hydrolysis
Esters

ASJC Scopus subject areas

  • Organic Chemistry

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Syntheses of indolyl-4(3H)-quinazolinones. / Hermecz, I.; Kökösi, J.; Podányi, Benjamin; Szász, G.

In: Heterocycles, Vol. 37, No. 2, 03.03.1994, p. 903-914.

Research output: Contribution to journalArticle

Hermecz, I. ; Kökösi, J. ; Podányi, Benjamin ; Szász, G. / Syntheses of indolyl-4(3H)-quinazolinones. In: Heterocycles. 1994 ; Vol. 37, No. 2. pp. 903-914.
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