Polycyclic N-heterocyclic compounds. Part 59: Rearrangement reactions of fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary amines via a Dimroth-type rearrangement

Kensuke Okuda; Hiromi Ohtomo; Fumiaki Tanaka; Takashi Hirota; Kenji Sasaki

doi:10.1248/cpb.57.755

Polycyclic N-heterocyclic compounds. Part 59: Rearrangement reactions of fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary amines via a Dimroth-type rearrangement

Kensuke Okuda, Hiromi Ohtomo, Fumiaki Tanaka, Takashi Hirota, Kenji Sasaki

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

2 Citations (Scopus)

Abstract

Reaction of some fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary alkyl amines gave abnormal fused 3-alkyl-4-alkyliminopyrimidines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. This abnormal rearrangement reaction depended on reaction solvent.

Original language	English
Pages (from-to)	755-758
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	57
Issue number	7
DOIs	https://doi.org/10.1248/cpb.57.755
Publication status	Published - Jul 2009

Keywords

3-alkyl-4-alkyliminopyrimidine
Dimroth rearrangement
Heterocycle
Pyrimidin-4(3H)-one
Tandem reaction

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.57.755

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Polycyclic N-heterocyclic compounds. Part 59 : Rearrangement reactions of fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary amines via a Dimroth-type rearrangement. / Okuda, Kensuke; Ohtomo, Hiromi; Tanaka, Fumiaki et al.

In: Chemical and Pharmaceutical Bulletin, Vol. 57, No. 7, 07.2009, p. 755-758.

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

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abstract = "Reaction of some fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary alkyl amines gave abnormal fused 3-alkyl-4-alkyliminopyrimidines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. This abnormal rearrangement reaction depended on reaction solvent.",

keywords = "3-alkyl-4-alkyliminopyrimidine, Dimroth rearrangement, Heterocycle, Pyrimidin-4(3H)-one, Tandem reaction",

author = "Kensuke Okuda and Hiromi Ohtomo and Fumiaki Tanaka and Takashi Hirota and Kenji Sasaki",

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AU - Ohtomo, Hiromi

AU - Tanaka, Fumiaki

AU - Hirota, Takashi

AU - Sasaki, Kenji

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N2 - Reaction of some fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary alkyl amines gave abnormal fused 3-alkyl-4-alkyliminopyrimidines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. This abnormal rearrangement reaction depended on reaction solvent.

AB - Reaction of some fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary alkyl amines gave abnormal fused 3-alkyl-4-alkyliminopyrimidines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. This abnormal rearrangement reaction depended on reaction solvent.

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KW - Heterocycle

KW - Pyrimidin-4(3H)-one

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Polycyclic N-heterocyclic compounds. Part 59: Rearrangement reactions of fused tricyclic 3-(2-bromoethyl)pyrimidin-4(3H)-ones with primary amines via a Dimroth-type rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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