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Synthesis of pyrido[2,3-d]pyrimidine (5-deazapteridine) C-nucleosides from a glycosyl enaminone

✍ Scribed by Isamu Maeba; Yasufumi Nishiyama; Masakazu Wakimura; Takayasu Tabata

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 366 KB
Volume: 290
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(96)00114-0

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✦ Synopsis

Increasing research has focused on examining the similarity between pyridopyrimidines and pyrimido [2,3-d]pyrazines, also referred to as pteridines [1]. Significant antitumor activity against Walker muscular carcinosarcoma in rats has been demonstrated for 4-oxopyrido [2,3-d]pyrimidine (A) and 2,4-dioxopyrido[2,3-d]pyrimidine (B) [2]. Robins and his collaborators [3] have synthesized 4-oxo-1-/3-oribofuranosylpyrido[2,3-d]pyrimidine and 2,4-dioxo-8-/3-D-ribofuranosyipyrido[2,3d]pyrimidine as potential antitumor and antiviral agents. Despite this, there are no reported examples of the synthesis of C-nucleosides of this ring system. The glycosyl enaminone 1 is a key synthetic intermediate in the synthesis of isoxazole [4], quinoline [5], and pyrazolo[1,5-a]pyrimidine [6] C-nucleosides, and can be obtained readily from 5-hydroxy-5-(2,3,5-tri-O-benzoyl-/3-D-ribofuranosyl)furan-2(5H)-one by our previously published procedure [7]. We wish to report here the utilization of 1 in the synthesis of pyrido[2,3-d]pyrimidine (5-deazapteridine) C-nucleosides.

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