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

Notes

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

Author information

Keywords: Dimroth rearrangement, 3-alkyl-4-alkyliminopyrimidine, pyrimidin-4(3H)-one, heterocycle, tandem reaction

JOURNAL FREE ACCESS

2009 Volume 57 Issue 7 Pages 755-758

DOI https://doi.org/10.1248/cpb.57.755

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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.

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