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

Institute for Education and Student Services

Research output: Contribution to journal › Article

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

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Heterocyclic Compounds

Amines

Methanol

Derivatives

Keywords

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

ASJC Scopus subject areas

Drug Discovery
Chemistry(all)

Cite this

Okuda, K., Ohtomo, H., Tanaka, F., Hirota, T., & Sasaki, K. (2009). 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. Chemical and Pharmaceutical Bulletin, 57(7), 755-758. https://doi.org/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. / Okuda, Kensuke; Ohtomo, Hiromi; Tanaka, Fumiaki; Hirota, Takashi; Sasaki, Kenji.

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

Research output: Contribution to journal › Article

Okuda, K, Ohtomo, H, Tanaka, F, Hirota, T & Sasaki, K 2009, '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', Chemical and Pharmaceutical Bulletin, vol. 57, no. 7, pp. 755-758. https://doi.org/10.1248/cpb.57.755

Okuda K, Ohtomo H, Tanaka F, Hirota T, Sasaki K. 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. Chemical and Pharmaceutical Bulletin. 2009 Jul;57(7):755-758. https://doi.org/10.1248/cpb.57.755

Okuda, Kensuke ; Ohtomo, Hiromi ; Tanaka, Fumiaki ; Hirota, Takashi ; Sasaki, Kenji. / 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. In: Chemical and Pharmaceutical Bulletin. 2009 ; Vol. 57, No. 7. pp. 755-758.

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10.1248/cpb.57.755