Photolyse von Adenin-1-N-Oxid

Purine N-oxides. LX. Photoreactions of 6-methyl- and 6,9-dimethylpurine 1-oxides

“…Found: C, 50.30; H, 4.94; N, 33.58. 2-Hydroxy-4-methylamino-5-nitro-6-methylpyrimidine (13). A solution of 11 (2.0 g, 10 mmol) in 10 ml of 1 TV NaOH was stirred in a H20 bath for 2 hr.…”

Novel Pschorr reaction in the papaverine series

“…one (8). 5 The oxoaporphine 8 presumably arises by the facile air oxidation of the unknown B-aromatic aporphine 9 during the work-up.6 HN0,…”

“…In an attempt to suppress the formation of indazole 7, 6'-aminopapaverine (5) was diazotized in 46% sulfuric acid. Decomposition of the diazonium salt with copper in the cold, followed by the usual work-up, gave none of indazole 7, but a mixture of the deamination product papaverine (10, 4.3%), a pale yellow compound C20H1SNO4 (30%), and an orange compound C19H10NO4 (2.4%).…”

“…2 The Pschorr procedure also takes an unexceptional course when applied to 6'-aminobenzoylisoquinolines, and affords a straightforward route to oxoaporphine alkaloids, i.e., liriodenine (3) from amino ketone 4. 3 2 In 1904, Pschorr reported a very different result when he diazotized a typical 6'-aminoisoquinoline, 6'-aminopapaverine (5). Loss of nitrogen did not occur, and Pschorr isolated the stable "diazopapaverine," which he formulated as the isoindazole 6. No aporphine-related substance was obtained.4 In this paper, we report a reinvestigation of the diazotization of 6'-aminopapaverine, including the conversion of this amine to a novel and hitherto unknown type of Pschorr reaction product.…”

A Versatile Synthetic Approach to Isoguanine Derivatives

“…These compounds were prepared from a substituted imidazole (usually a 5-amino-4-carbamoyl imidazole 4,5 or a 4,5dicyanoimidazole 5 ) or from a substituted purine, in several consecutive steps. 2-Aminoadenosine, 6 adenosine N-1oxide, 7 guanosine, 8 2-amino-6-chloropurine 9 or 2-oxo-6chloropurine 10 are some examples of purine compounds that have been used in these synthesis.…”