By Alan R. Katritzky
Demonstrated in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of significant significance to natural chemists, polymer chemists, and so much organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry incorporates a cumulative topic index.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 4
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. g. the dihydropyridines, 61 W. L. F. Armarego, J . Chem. 6073 (1963). 38 ADRIEN ALBERT AND W. L. F. ARMAREGO [Sec. V. dihydropyrans, and dihydropyrroles) add water much more readily, but this behavior is far less remarkable.
L. F. ARMAREOO [Sec. 111. 2 1. Quinazoline The anomalous behavior of quinazoline was first discovered by Albert et ~ 1 who . 5). Mason36 then observed that the ultraviolet spectrum of the quinazoline cation was abnormal but that the spectrum of 4-methylquinazoline was normal (see Fig. 2). These anomalies led to the suggestion that water adds covalently to the cation of quinazoline30*37 to give 12 (R = H). The occurrence and position of hydration were confirmed l 2 by a detailed study of the ultraviolet and infrared spectra of the anhydrous and hydrated hydrochlorides and by mild oxidation of the cation to 4(3H)-quinazolinone.
E. Willette, J . ,in press. 408 W. Sec. 111. 11 COVALENT HYDRATION: I. QUALITATIVE ASPECTS 23 higher acidities which are necessary (because of the lower pK, values) to protonate the N-oxide molecules have a dehydrating effect. l6 D. TRIAZANAPHTHALENES 1. 1,3,~-Triazanaphthulenes These compounds are discussed in two separate groups: (a)the 1,2,3- and 1,2,4-triazanaphthalenes,and ( b ) the 1,3,5-, 1,3,6-, 1,3,7-, and 1,3,8-triazanaphthalenes. (a)1,2,3-Triazanaphthalene has not been prepared but several observations 41 suggest that it would behave as an unstable diazonium compound.
Advances in Heterocyclic Chemistry, Vol. 4 by Alan R. Katritzky