Quinazolin-2-ones Having a Spirohydantoin Ring.I

Reaction of 1-methylcarbamoylisation (4) with urea in the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 4-hydroxy-3-methyl-4-ureidocarbonyl-1, 2, 3, 4-tetrahydroquinazolin-2-one (5), which was easily cyclized with 10% HCl to afford a spirohydantoin derivative; 3-methyl-spiro[1, 2, 3, 4-...

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Published inChemical & pharmaceutical bulletin Vol. 38; no. 11; p. 2926
Main Authors YAMAGISHI, Masafumi, OZAKI, Ken-ichi, OHMIZU, Hiroshi, YAMADA, Yoshihisa, SUZUKI, Mamoru
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 01.11.1990
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Abstract Reaction of 1-methylcarbamoylisation (4) with urea in the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 4-hydroxy-3-methyl-4-ureidocarbonyl-1, 2, 3, 4-tetrahydroquinazolin-2-one (5), which was easily cyclized with 10% HCl to afford a spirohydantoin derivative; 3-methyl-spiro[1, 2, 3, 4-tetrahydroquinazoline-4, 4'-imidazolidine]-2, 2', 5'-trione (6). In a similar manner, 2'-imino-3-methyl-spiro[1, 2, 3, 4-tetrahydroquinazoline-4.4'-imidazolidine]-2, 5'-dione (8) was prepared by the reaction of 4 with guanidine, and 8 was further converted to the spirohydantoin compound 6 by treatment with sodium nitrite in acetic acid.
AbstractList Reaction of 1-methylcarbamoylisation (4) with urea in the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave 4-hydroxy-3-methyl-4-ureidocarbonyl-1, 2, 3, 4-tetrahydroquinazolin-2-one (5), which was easily cyclized with 10% HCl to afford a spirohydantoin derivative; 3-methyl-spiro[1, 2, 3, 4-tetrahydroquinazoline-4, 4'-imidazolidine]-2, 2', 5'-trione (6). In a similar manner, 2'-imino-3-methyl-spiro[1, 2, 3, 4-tetrahydroquinazoline-4.4'-imidazolidine]-2, 5'-dione (8) was prepared by the reaction of 4 with guanidine, and 8 was further converted to the spirohydantoin compound 6 by treatment with sodium nitrite in acetic acid.
Author OHMIZU, Hiroshi
YAMAGISHI, Masafumi
YAMADA, Yoshihisa
SUZUKI, Mamoru
OZAKI, Ken-ichi
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