Advances in Heterocyclic Chemistry, Vol. 24 by A.R. Katritzky PDF

By A.R. Katritzky

ISBN-10: 0120206242

ISBN-13: 9780120206247

(from preface)This quantity makes an immense 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 longer we intend to up-date chapters from 10 to fifteen years after their visual appeal, only if substantial paintings has been conducted within the sector covered.Five chapters were up-dated by means of the authors of the unique chapters that seemed in previous volumes, as follows: Quinazolines, by way of W. L. F. Armarego (the unique bankruptcy seemed in quantity 1), 3-membered earrings with Heteroatoms, by way of E. Schmitz (Volume 2), Physicochemical facets of Purines, through J. H. Lister (Volume 6), Reis-sert Compounds, through F. D. Popp (Volume 9), and Pyridazines, via M. Tiffler and B. Stanovnik (Volume 9).Two different chapters up-date matters coated in previous volumes, yet through diverse authors: Selenium-Nitrogen Heterocycles, through I. Lalezari, A. Shafiee, and M. Yalpani, which up-dates the contribution through Bulka in quantity 2 on Selenazole Chemistry, and Pyrrolizidines, by way of D. J. Robins, which up-dates the contribution by means of Kochetkov and Likhosherstov in quantity 5.Finally, chapters care for considerably new themes: Benzo[c]cin-nolines, by means of J. W. Barton, and 1, 4-Thiazines, through R. J. Stoodley.

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Chupakhin, and I . Ya. Postovskii, K\7im. Geterotsikl. , 561 (1975). K. Lempert and P. Gyulai, Trtruhedron 26, 3443 (1970). 38 [Sec. A W. L . F. l9l The imines 71, in the latter reaction, required a temperature of 125°C for several days to give the 4-methylene-3,4-dihydroquiaazolines (72)in ca. 50% yields. Quinazolines could not be formed in this reaction when both the ortho positions of the N-aryl group were substituted. R Ph Me OH (73) (74) Ring cleavage caused by the addition of Grignard reagents to quinazolin4(3H)-ones has been mentioned earlier (Section TV,C).

C. Taylor, M. L. Chittenden, and S. F. Martin, Heterocycles 1. 59 (1973). 13' 139 A. Sec. E] 29 QUINAZOLINES 4-p-Tosylquinazoline was readily converted into 4-cyanoquinazoline (KCN, DMF),'44 and 2-fluorosulfonyl- and 4-sulfoquinazolines gave the ~~ respective 2- and 4-hydrazinoquinazoline with h ~ d r a z i n e . 147This reaction can be usefully adapted for the preparation of deuterated derivatives if deuterated solvents are used. The kinetics of deamination of 4-aminoquinazoline to quinazolin-4(3H)one was studied in detail at various potassium hydroxide concentrations.

Pliurm. Jugosl. 25, 223 (1975) [CA 84, 121762 (1976)l. 1 7 6 F. Gatta and R. Landi Vittory, G a z . Cliim. I t d . 99, 715 (1969). 177 17' 17' Is' Is' K. Okumura, T. Oine, Y . Yamada, G. Hayashi, and M. Nakama, J. Med. Cliem. 11, 348 (1968). K. Okumura, T. Oine, Y . Yamada, G. Hayashi, M . Nakama, and T. Nose, J . Med. Clzem. 11, 788 (1968). H. Mohrle and C . M. Seidel, Arch. Pliurni. (Weinhein7)309. 572 (1976). P. de Mayo and J. J . Ryan, Chem. , 88 (1967). J. W. S. Perkin I, 2004 (1976); G. F.

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