4(3H)-Quinazolinones containing heterocyclic group in position 3

Tonkikh, N. N.; Петрова, М. В.; Mishnev, Anatoly; Ryzhanova, K. V.; Avotin'sh, F. M.; Strakov, A. Ya.

doi:10.1007/bf02256917

Cited by 3 publications

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“…21 A variety of 2,3-disubstituted 4(3H)-quinazolinones containing a heterocyclic group in position 3 have been prepared from the reaction of 2-methyl and 2-phenyl-(4H)-3,1-benzoxazinones with different heterocycles containing the amino functionality. 22 Various quinazolinone dyes have been synthesized from coupling diazotized aminoquinazolinone with various coupling components and their dyeing effect on viscose rayon, silk and wool fibers has been assessed. 23 The forementioned findings prompted the author to carry out the reaction of 1a…”

Section: Resultsmentioning

confidence: 99%

Reactivity of 4H-3,1-benzoxazin-4-ones towards nitrogen and carbon nucleophilic reagents: applications to the synthesis of new Heterocycles

Madkour¹

2004

Arkivoc

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6,8-Dibromo-(4H)-3,1-benzoxazinone 1a was synthesized and allowed to react with some nitrogen nucleophiles namely, hydroxylamine hydrochloride, 4-aminoacetophenone, ophenylenediamine, sulfanilamide, sulfamethoxazole, semicarbazide hydrochloride and ethanolamine to afford 3-substituted-4(3H)-quinazolinones 2-8, 10-12 and triazolo[2,3-c]quinazoline 9. 6-Bromo(4H)-3,1-benzoxazin-4-one 1b was also synthesized and converted into 3-amino-4(3H) quinazolinone 13 by reaction with hydrazine hydrate. The latter product was utilized to construct new heterocyclic systems namely, triazino[2,3-c] quinazoline 14 and the thiazole derivative 16. An interesting heterocyclic transformation occurred on treatment of benzoxazinone 1a with malononitrile in presence of sodium ethoxide to give quinoline derivative 18 which reacted with phenyl isocyanate to yield oxazinoquinoline 19. The reaction of benzoxazinone 1a with Grignard' reagents afforded unexpected products 20 and 21 whereas Friedel-Crafts reaction of the same oxazinone with some aromatic hydrocarbons namely, benzene, ethylbenzene, m-and p-xylenes afforded either two benzophenone derivatives 20 and 22 or 23 and 24 in case of less bulky hydrocarbons i.e., benzene and ethylbenzene or only one product 25 and 26 in case of more bulky m-and p-xylenes. Oxazinone ring cleavage occurred when barbituric and/or thiobarbituric acid reacted with benzoxazinone 1a in refluxing pyridine to give the corresponding 5-arylidene derivatives 27a,b.

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Section: Resultsmentioning

confidence: 99%

Reactivity of 4H-3,1-benzoxazin-4-ones towards nitrogen and carbon nucleophilic reagents: applications to the synthesis of new Heterocycles

Madkour¹

2004

Arkivoc

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ChemInform Abstract: 4(3H)‐Quinazolinones Containing Heterocyclic Group in Position 3.

et al. 2001

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fused pyrimidine derivatives fused pyrimidine derivatives R 0515 21 -139 4(3H)-Quinazolinones Containing Heterocyclic Group in Position 3. -Reaction of 2-methylbenzoxazinone (I) with heterocyclic amines (II) gives the corresponding 2-methylquinazolinones (III) (6 examples), while 2-phenylbenzoxazinone (IV) furnishes the corresponding 2-phenylquinazolinones (V) or N-benzoylanthranilamides (VI) depending on the amine (II) employed. -(TONKIKH, N. N.; PETROVA, M. V.; MISHNEV, A. F.; RYZHANOVA, K. V.; AVOTIN'SH, F. M.; STRAKOV, A. YA.; Chem. Heterocycl.

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