8-Quinolyl phosphate

The base hydrolysis under harsh conditions very often brings about undesired cleavage of phosphates. In contrast, removal of an o- orp-chlorophenyl protecting group by lV ,iV, iV, /V -tetramethylguanidinium ryn-p-nitrobenzaldoxymate (NBO) (108 equation 65) or syn-pyridin-2-aldoxymate (PAO) (109) is achievable at room temperature and no side reaction occurs. The 8-quinolyl phosphate (110 equation 66) is also hydrolyzed under mild conditions with the assistance of a stoichiometric amount of ZnCb or CuCb salt. ... 

Amino-l-methylbutyl) amino]-6-methoxy quinoline phosphate (1 2) 1,4-Pentanediamine, N -(6-methoxy-8-quinolyl)-, phosphate (1 2) Primachin phosphate BP USP Int. P. Primaquine Phosphate (ICl Pharmaceuticals, U.K.)... 

Hydrolysis of 8-quinolyl phosphate (98) (8QP) in the presence of trivalent lanthanides (Ln-La, Sm, Eu, Tb, and Er) proceeded through formation of an [Ln 8QP] complex that decomposed into the product (99) (Scheme 21)." The lanthanides favored a single-step DnAn mechanism with a dissociative transition state, a limited nucleophilic assistance, a low hydroxide ion dependence and a small kinetic effect of Ln radii. 

Cheng et al. [116] reported that the structure of primaquine phosphate irradiated with 0.7—10 Mrad remained unchanged. The energy transfer action of the quinolyl group was considerable due to its resonance stabilization. Radiation-induced degradation of polyl(vinyl alcohol) decreased in the presence of primaquine phosphate but the degradation mechanism was unaffected. The content of primaquine phosphate showed linear relationship with degradation parameters of poly(vinyl alcohol). 

Chemical Synthesis.—Two new methods for 5 -phosphorylation of nucleosides have been described. In the first, phosphorous acid and mercuric chloride are heated at 80 °C in iV-methylimidazole, and a 2, 3 -0-isopropylidene-protected nucleoside is added. On work-up the 5 -phosphate is obtained in 60— 70% yield. The phosphorylating agent is presumed to be an iV-phosphoryl-AT -methylimidazolium species (1). The second method employs tris-(8-quinolyl)... 

Benzyl 8-quinolyl hydrogen phosphate heated 5 hrs. at 70° with ethanol and CuClg in anhydrous pyridine benzyl ethyl phosphate. Y 90% as the Ba-salt. F. e., also phosphoric acid monoesters, and sym. diphosphoric acid diesters with cupric acetate, s. K. Nagasawa and H. Yoshidome, Chem. Pharm. Bull. 20, 1840 (1972) s. a. H. Takaku, Y. Shimada, and K. Aral, Bull. Chem. Soc. Japan 47, 779 (1974). 

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