Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II

Masatoshi Yamato; Jiroh Horiuchi; Yasuo Takeuchi

doi:10.1248/cpb.29.3055

Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II

Masatoshi Yamato, Jiroh Horiuchi, Yasuo Takeuchi

研究成果 › 査読

1 被引用数 (Scopus)

抄録

The reaction of 1,2,3,4-tetrahydroquinazoline-2-spirocyclohexan-4-one (1b) with acetic anhydride and pyridine gave 1-(1-cyclohexenyl)-2-methyl-1,4-dihydroquinazolin-4-one (3b). Compound 3b gave 3-acetyl-1-(1-cyclohexenyl)-2-methyl-1,2,3,4-tetrahydroquinazolin-4-one (8b) upon reduction with NaBH₄ followed by acetylation with acetic anhydride. The position of the acetyl group of 8b was determined by comparison of its NMR spectrum with those of related compounds (9, 10, 11, 12, and 13).

本文言語	English
ページ（範囲）	3055-3059
ページ数	5
ジャーナル	Chemical and Pharmaceutical Bulletin
巻	29
号	10
DOI	https://doi.org/10.1248/cpb.29.3055
出版ステータス	Published - 1981

ASJC Scopus subject areas

化学 (全般)
創薬

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10.1248/cpb.29.3055

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title = "Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II",

abstract = "The reaction of 1,2,3,4-tetrahydroquinazoline-2-spirocyclohexan-4-one (1b) with acetic anhydride and pyridine gave 1-(1-cyclohexenyl)-2-methyl-1,4-dihydroquinazolin-4-one (3b). Compound 3b gave 3-acetyl-1-(1-cyclohexenyl)-2-methyl-1,2,3,4-tetrahydroquinazolin-4-one (8b) upon reduction with NaBH4 followed by acetylation with acetic anhydride. The position of the acetyl group of 8b was determined by comparison of its NMR spectrum with those of related compounds (9, 10, 11, 12, and 13).",

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author = "Masatoshi Yamato and Jiroh Horiuchi and Yasuo Takeuchi",

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T1 - Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II

AU - Yamato, Masatoshi

AU - Horiuchi, Jiroh

AU - Takeuchi, Yasuo

PY - 1981

Y1 - 1981

N2 - The reaction of 1,2,3,4-tetrahydroquinazoline-2-spirocyclohexan-4-one (1b) with acetic anhydride and pyridine gave 1-(1-cyclohexenyl)-2-methyl-1,4-dihydroquinazolin-4-one (3b). Compound 3b gave 3-acetyl-1-(1-cyclohexenyl)-2-methyl-1,2,3,4-tetrahydroquinazolin-4-one (8b) upon reduction with NaBH4 followed by acetylation with acetic anhydride. The position of the acetyl group of 8b was determined by comparison of its NMR spectrum with those of related compounds (9, 10, 11, 12, and 13).

AB - The reaction of 1,2,3,4-tetrahydroquinazoline-2-spirocyclohexan-4-one (1b) with acetic anhydride and pyridine gave 1-(1-cyclohexenyl)-2-methyl-1,4-dihydroquinazolin-4-one (3b). Compound 3b gave 3-acetyl-1-(1-cyclohexenyl)-2-methyl-1,2,3,4-tetrahydroquinazolin-4-one (8b) upon reduction with NaBH4 followed by acetylation with acetic anhydride. The position of the acetyl group of 8b was determined by comparison of its NMR spectrum with those of related compounds (9, 10, 11, 12, and 13).

KW - 4-quinazoline

KW - H-NMR

KW - acetylation

KW - rearrangement

KW - spiro compound

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JO - Chemical and Pharmaceutical Bulletin

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Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II

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