By Alan R. Katritzky
Verified in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of serious significance 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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Extra resources for Advances in Heterocyclic Chemistry, Vol. 4
GENERALDISCUSSION Covalent hydration has not been demonstrated in heteroaromatic compounds containing only one hetero atom, nor in systems which possess other hetero atoms in addition t o nitrogen. g. acetylacetone, ethyl malonate, the cyanide ion, and Grignard reagents) to substances which are readily hydrated such as 2-hydro~ypteridine,~l 6-hydroxypteridine, quinazoline,18 and quinazoline 3-oxide28a always takes place across the same C=N bond to which the water molecule adds. g. a ~ r i d i n e30, ~q ~ i~n o x a l i n eand , ~ ~even, perhaps, quinoline 32) would form covalent hydrates.
Albert, D. J. Brown, and H. C. S. Wood, J . Chem. 3832 (1954). 36A. R. Osborn, K. Schofield, and L. N. Short,J. Soc. 4191 (1956). 37 A. Albert, Chem. SOC. (London) Spec. Publ. No. 3, 138 (1955). 38 D. J. Fry, J. D. Kendall, and A. J. Morgan, J . Chem. SOC. 6062 (1960). 36 Sec. 111. 21 COVALENT HYDRATION: I. 5 x (determined as described in the following review lo), but the derivatives have somewhat different values depending on the position and nature of the substituent. 8 x and 10 x respectively, indicating the electronattracting property of the nitro group.
1,3,6Triazanaphthalene, under the same conditions, gave a yellow precipitG. Erickson, P. F. Wiley, and V. P. ” Wiley, New York, 1966. 4 1 J. 24 ADRIEN ALBERT AND w. L. F. ARMAREQO [Sec. 111. l ate of the hydrazone after 3 min. 14 As in the neutral species (above), hydration in the cations of 1,3,5-, 1,3,7-, and 1,3,8-triazanaphthalenesis followed by slow ring-opening, but the amount of ring-opened product is negligibly small in the first 30 min, allowing enough time for accurate determination of the ionization and rate constants.
Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky