A remarkable case of pterin specific oxidative coupling: unequivocal synthesis of 6, 7-alkoxypterins and 1, 4-dioxanopterin with ceric ammonium nitrate. Issue 30 (27th July 2016)

• Record Type: Journal Article
• Authors: Das, Manas Kumar; Goswami, Shyamaprosad; Quah, Ching Kheng; Fun, Hoong-Kun
• Is Part Of: Tetrahedron letters. Volume 57:Issue 30(2016)
• Page Start: 3277
• Page End: 3280
• Publication Date: 2016-07-27
• Subjects: Alkoxy pterin -- 1, 4-Dioxano pterin -- Ceric ammonium nitrate -- Ethylene glycol; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.031
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: First report of efficient alkoxylation onto pterins using ceric ammonium nitrate. This method is specific to pteridine or deazapterin system at 6 and 7 positions. Direct 6, 7-functionalization onto pterins is difficult. Thus this method is useful for direct 6, 7-functionalization. CAN is also found to be a specific reagent for such oxidative alkoxylation onto pteridines. Abstract: A facile and efficient synthesis of a series of methoxy and ethoxy substituted pterins (characterized by single crystal X-ray structures of 6, 7-dimethoxy and diethoxy-pterins) along with 1, 4-dioxanopterin is reported along with a possible mechanism for their formation by treatment of pterins with ceric ammonium nitrate in methanol, ethanol, and ethylene glycol respectively. This unequivocal alkoxylation is unique only with pterin (and 5-deaza-pterin) and is unsuccessful with quinoxaline.