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

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

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).

Original language	English
Pages (from-to)	3055-3059
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	29
Issue number	10
DOIs	https://doi.org/10.1248/cpb.29.3055
Publication status	Published - 1981

Keywords

4-quinazoline
H-NMR
acetylation
rearrangement
spiro compound

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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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).",

keywords = "4-quinazoline, H-NMR, acetylation, rearrangement, spiro compound",

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

year = "1981",

doi = "10.1248/cpb.29.3055",

language = "English",

volume = "29",

pages = "3055--3059",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "10",

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TY - JOUR

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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DO - 10.1248/cpb.29.3055

M3 - Article

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SN - 0009-2363

VL - 29

SP - 3055

EP - 3059

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 10

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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