By A.R. Katritzky
(from preface)This quantity makes an enormous contribution to the method of up-dating past volumes that we have got initiated. Seven of the 9 chapters are dedicated to this function and any further we intend to up-date chapters from 10 to fifteen years after their visual appeal, only if substantial paintings has been performed within the region covered.Five chapters were up-dated through the authors of the unique chapters that seemed in past volumes, as follows: Quinazolines, through W. L. F. Armarego (the unique bankruptcy seemed in quantity 1), 3-membered earrings with Heteroatoms, via E. Schmitz (Volume 2), Physicochemical features of Purines, via J. H. Lister (Volume 6), Reis-sert Compounds, by way of F. D. Popp (Volume 9), and Pyridazines, by way of M. Tiffler and B. Stanovnik (Volume 9).Two different chapters up-date matters coated in past volumes, yet via varied authors: Selenium-Nitrogen Heterocycles, via I. Lalezari, A. Shafiee, and M. Yalpani, which up-dates the contribution by means of Bulka in quantity 2 on Selenazole Chemistry, and Pyrrolizidines, via D. J. Robins, which up-dates the contribution by way of Kochetkov and Likhosherstov in quantity 5.Finally, chapters care for considerably new subject matters: Benzo[c]cin-nolines, through J. W. Barton, and 1, 4-Thiazines, by way of R. J. Stoodley.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 24
Five main products were isolated and characterized from acidic solutions. These were o-aminobenzaldehyde, the anhydro trimer (31: R1= H, R2 = OH), the anhydro tetramer [31: R' = H; RZ = -NHC6H4CHO(o)], the monoformyl tetramer [31: R 1 = CHO; RZ = -NHC,H,CHO(o)], and substance Q. Substance Q was shown to be a polymer of the addition loo A. AIbert and H . Yamamoto, J. Chem. C , 1944 (1968). Sec. A] QUINAZOLINES 21 product (32) of o-aminobenzaldehyde and quinazoline. 5. Quinazolin-4(3H)-ones are not readily degraded by reagents in alkaline media because they form stable anions.
M. Sheepy, J. Org. Chem. 42, 78 (1977). C. Bogentoft, L. Kronberg, and B. Danielsson, Acta Pharm. Suer. 6, 489 (1969) [CA 72, I1916 (1970)l. G . Wagner and F. Suess, Pharmazie 24, 35 (1969). Sec. C] 23 QUINAZOLINES a-bromoketones at N-1, and products were then hydrolyzed by acid or base to N - 1 acylmet hylquinazolin-4-ones. "' (40)R = H,D C. ADDITION REACTIONS The addition of water (see Section II,B) and other nucleophiles across the 3,4-double bond of quinazoline is well established. More recently other nucleophiles, such as dimedone, have given isolable 3,4-adducts.
However, if the tautomeric hydrogen is substituted, then the heterocyclic ring becomes susceptible to cleavage. "' The second lo' C. Bogentoft, 0. Ericsson, P. Stenberg, and B. , 4745 (1969). 22 W. L. F. lo2 B. ALKYLATION For many years it was assumed that alkylation of quinazoline with methyl iodide gave only 3-methylquinazolinium iodide. ' O6 These anions produced methyl derivatives, on treatment with methyl iodide, which gave some indication of where the negative charges were located in the molecule (see further discussion in Section V1,A).
Advances in Heterocyclic Chemistry, Vol. 24 by A.R. Katritzky