Unexpected Observation of the Dimroth Rearrangement in the Ribosylation of 4‑Aminopyrimidines

Unexpected Observation of the Dimroth Rearrangement in the Ribosylation of 4‑Aminopyrimidines

A method for the preparation of 1-(N-ribofuranosyl)-6-imino-1,6-dihydropyrimidin-4-amines 3 or 4-(N-ribofuranosyl)-6-aminopyrimidines 4 via glycosylation of 4-aminopyrimidines 2 or 5 is described. Silylated 4-aminopyrimidines 2 or 5 upon ribosylation with 1 provide products 3. When intermediates 3 c...

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Veröffentlicht in:Journal of organic chemistry 2017-06, Vol.82 (11), p.5881-5889
Hauptverfasser: Baiazitov, Ramil Y, Sydorenko, Nadiya, Ren, Hongyu, Moon, Young-Choon
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container_end_page 5889
container_issue 11
container_start_page 5881
container_title Journal of organic chemistry
container_volume 82
creator Baiazitov, Ramil Y
Sydorenko, Nadiya
Ren, Hongyu
Moon, Young-Choon
description A method for the preparation of 1-(N-ribofuranosyl)-6-imino-1,6-dihydropyrimidin-4-amines 3 or 4-(N-ribofuranosyl)-6-aminopyrimidines 4 via glycosylation of 4-aminopyrimidines 2 or 5 is described. Silylated 4-aminopyrimidines 2 or 5 upon ribosylation with 1 provide products 3. When intermediates 3 contain a strongly electron-withdrawing group, such as C(4)-Cl or C(5)-NO2, they rearrange to products 4 in the presence of aqueous ammonia. A mechanism is proposed that involves a ring-opening/ring-closing (Dimroth) rearrangement.
doi_str_mv 10.1021/acs.joc.7b00780
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title Unexpected Observation of the Dimroth Rearrangement in the Ribosylation of 4‑Aminopyrimidines
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