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

Jiroh Horiuchi; Yasuo Takeuchi; Masatoshi Yamato

doi:10.1248/cpb.29.3130

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

Jiroh Horiuchi, Yasuo Takeuchi, Masatoshi Yamato

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

5 Citations (Scopus)

Abstract

The reaction of 2-substituted 1-methyl-1,2,3,4-tetrahydroquinazolin-4-ones (THQ) with acetic anhydride afforded two types of products depending on the number of C₂-substituents. The reaction of 2-monosubstituted 1-methyl-THQ (6) gave the corresponding N₃-acetyl-THQ derivatives (7), while the reaction of 2,2-disubstituted 1-methyl-THQ (8) afforded rearranged products, 2,3-disubstituted 1-methyl-1,4-dihydroquinolin-4-ones (9). A mechanism is proposed for the reaction of 8 to give 9.

Original language	English
Pages (from-to)	3130-3133
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	29
Issue number	11
DOIs	https://doi.org/10.1248/cpb.29.3130
Publication status	Published - 1981

Keywords

1,2,3,4-tetrahydroquinazolin-4-ones
1,4-dihydroquinolin-4-ones
acetic anhydride
acetylation
rearrangement

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.29.3130

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

abstract = "The reaction of 2-substituted 1-methyl-1,2,3,4-tetrahydroquinazolin-4-ones (THQ) with acetic anhydride afforded two types of products depending on the number of C2-substituents. The reaction of 2-monosubstituted 1-methyl-THQ (6) gave the corresponding N3-acetyl-THQ derivatives (7), while the reaction of 2,2-disubstituted 1-methyl-THQ (8) afforded rearranged products, 2,3-disubstituted 1-methyl-1,4-dihydroquinolin-4-ones (9). A mechanism is proposed for the reaction of 8 to give 9.",

keywords = "1,2,3,4-tetrahydroquinazolin-4-ones, 1,4-dihydroquinolin-4-ones, acetic anhydride, acetylation, rearrangement",

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

year = "1981",

doi = "10.1248/cpb.29.3130",

language = "English",

volume = "29",

pages = "3130--3133",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "11",

}

TY - JOUR

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

AU - Horiuchi, Jiroh

AU - Takeuchi, Yasuo

AU - Yamato, Masatoshi

PY - 1981

Y1 - 1981

N2 - The reaction of 2-substituted 1-methyl-1,2,3,4-tetrahydroquinazolin-4-ones (THQ) with acetic anhydride afforded two types of products depending on the number of C2-substituents. The reaction of 2-monosubstituted 1-methyl-THQ (6) gave the corresponding N3-acetyl-THQ derivatives (7), while the reaction of 2,2-disubstituted 1-methyl-THQ (8) afforded rearranged products, 2,3-disubstituted 1-methyl-1,4-dihydroquinolin-4-ones (9). A mechanism is proposed for the reaction of 8 to give 9.

AB - The reaction of 2-substituted 1-methyl-1,2,3,4-tetrahydroquinazolin-4-ones (THQ) with acetic anhydride afforded two types of products depending on the number of C2-substituents. The reaction of 2-monosubstituted 1-methyl-THQ (6) gave the corresponding N3-acetyl-THQ derivatives (7), while the reaction of 2,2-disubstituted 1-methyl-THQ (8) afforded rearranged products, 2,3-disubstituted 1-methyl-1,4-dihydroquinolin-4-ones (9). A mechanism is proposed for the reaction of 8 to give 9.

KW - 1,2,3,4-tetrahydroquinazolin-4-ones

KW - 1,4-dihydroquinolin-4-ones

KW - acetic anhydride

KW - acetylation

KW - rearrangement

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U2 - 10.1248/cpb.29.3130

DO - 10.1248/cpb.29.3130

M3 - Article

AN - SCOPUS:0019766822

SN - 0009-2363

VL - 29

SP - 3130

EP - 3133

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 11

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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