By Alan R. Katritzky

ISBN-10: 0120206048

ISBN-13: 9780120206049

Confirmed in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of serious value to natural chemists, polymer chemists, and such a lot organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry incorporates a cumulative topic index.

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These two substances are to be contrasted with equally electrondeficient substances which form strongly resonant hydrates, viz. quinazoline l 2 and 1,3,5-triazanaphthaIene, l 4 respectively. g. -NH2, -OH) diminish or prevent covalent hydration by decreasing the electron deficiency in the nucleus. g. the ureatype resonance and the 4-aminopyridine-type resonance in 2- and 6-hydroxypteridine, respectively. g. g. 43. Thus far, this section has been concerned with the explanation of the factors responsible for the covalent hydration of heteroaromatic substances.

1N sodium hydroxide at room temperature has been used to oxidize 2- and 6-hydroxypteridine to 2,4- and 6,7-dihydroxypteridine, respectively. In contrast, 4-hydroxypteridine was not attacked by this reagent even at 100’. Hydrogen peroxide in acid solution was used to oxidize quinazoline l 2; quinazoline 3-oxidel e ; 1,3,5-, 1,3,7-, and 1,3,8-triazanaphthalene 1 4 ; and ~ t e r i d i n e(which ~ ~ hydrate across the 3,4-double bond in the Y . Inoue end D. D. Perrin, J . SOC. 4803 (1963). A. Albert and C.

8. l 4 ( b ) 1,3,5-, 1,3,6-, 1,3,7-, and 1,3,8-Triazanaphthaleneshave been studied in detail, and their neutral species were shown to be predominantly anhydrous. 20 x respectively. 3 x value for 1,3,6-triazanaphthalene could be measured because the compound decomposed rapidly in acid solution. 14The other three triazanaphthalenes were very stable under the same conditions, but they decomposed rapidly in N-sodium hydroxide. The spectra of 1,3,5-, 1,3,7-, and 1,3,8-triazanaphthalene cations revealed that they were predominantly hydrated, and mild oxidation to the corresponding 4-0x0 compounds indicated that hydroxylation took place on C-4.

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Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky


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