Pyrido pyrimidines spectra

Mason has determined the infrared spectrum of pyrido[3,2-d]-pyrimidin-4(3ff)-one (149, N in position 5) in chloroform solution and as a KBr disc and has suggested that the low frequency of th e NH band (3389 cm ) and high frequency of the C=0 band (1745 cm i) in the solution spectra are indicative of a quasi o-quinonoid form. The infrared spectra of the four pyridopyrimidin-4(377)-ones (149), the four 2,4(ljff,3//)-diones (150), and a number of substituted derivatives, have been determined, as Nujol mulls, in these laboratories. ... 

The absolute configuration of C-3 of the chromophore 459 of isopyoverdins was determined to be S from the circular dichroism (CD) spectrum (Cotton effect +242 nm, —290 nm, +358 nm) of 460 obtained from isopyoverdin by acidic hydrolysis <2001T1019>. Diorganotin(iv) complexes with 4//-pyrido[l,2-/z pyrimidin-4-ones 461 <1996AOM47>, complexes of 2-methyl- and 2-methyl-8-nitro-9-hydroxy-4//-pyrido[l,2-tf]pyrimidin-4-ones with Ag(i), Cu(ll), Ni(n), Co(n), and Mn(n) ions <2000RJD587>, 2,4-dimethyl-9-hydroxypyrido[l,2-tf]pyrimidinium perchlorate and its complexes with prasedynium, neodymium, samarium, and europium <2000RJD310> were characterized by UV spectroscopy. 

Kato et al.19 compared the mass spectra of 2-methyl-4-oxo-4/7- and 4-methyl-2-oxo-2//-pyrido[l,2-a]pyrimidines. Fragments at m/e = 120 and 92 appeared only in the spectrum of the 2-oxo isomer. In the spectrum of the 4-oxo isomer the peak at m/e = 105 corresponds to a single fragment of composition C6H5N2, whereas for the 2-oxo isomer, it is a mixture of two fragments, C6H5N2 and C7H7N. 

Comparison of the spectral data on the isomeric 4-oxo-47/-pyrido-[1,2-a]pyrimidines and 4-oxo-l,4-dihydro-l,8-naphthyridines revealed that in the UV spectrum the highest wavelength maximum is generally situated... 

The structure of the reaction product of 2-aminopyridine and diethyl malonate, described by Chichibabin as 2,4-dioxo-3,4-dihydro-2//-pyrido-[l,2-<7]pyrimidine,96 was first questioned by Snyder and Robison253 on the basis of the high melting point and poor solubility of the compound. They suggested the tautomeric 2-hydroxy-4-oxo-4H-pyrido[l,2-a]pyrimidine structure. The problem was solved by Katritzky and Waring273 who compared the UV spectrum of the product with that of fixed tautomers and found that the product may best be described as anhydro- 2-hydroxy-4-oxo-4/f-pyrido[l,2- ]pyrimidinium)hydroxide (63). Because of the chemical behavior of these compounds, however, the contribution of other mesomeric forms to the structure has also been considered.122 Thus, PPP-SCF quantum chemical calculations suggest that 1,4-dipolar cycloadditions to the C-3 and C-9a atoms are to be expected.352 This type of reaction does in fact occur (see Section III,C,10). Katritzky and Waring273 estimated the ratio of the mesomeric betaine (63 R = H) and the 2-hydroxy-4-oxo tautomers to be about 20 1. 

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