By A.R. Katritzky

(from preface)This quantity makes a huge contribution to the method of up-dating past volumes that we've 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 significant paintings has been performed within the zone covered.Five chapters were up-dated by means of the authors of the unique chapters that seemed in previous volumes, as follows: Quinazolines, via W. L. F. Armarego (the unique bankruptcy seemed in quantity 1), 3-membered jewelry with Heteroatoms, by way of E. Schmitz (Volume 2), Physicochemical elements of Purines, via 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 topics coated in prior volumes, yet by way of various authors: Selenium-Nitrogen Heterocycles, by way of I. Lalezari, A. Shafiee, and M. Yalpani, which up-dates the contribution via Bulka in quantity 2 on Selenazole Chemistry, and Pyrrolizidines, by means of 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, by way of J. W. Barton, and 1, 4-Thiazines, through R. J. Stoodley.

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Chrm. C , 2502 (1971). 46 [Sec. A W. L. F. ’18,’19 VII. Molecular Rearrangements and Ring Transformations Involving Quinazolines Molecular rearrangements in which quinazolines are the reactants or the products are discussed in this section. The section is divided into three parts according to the effect that the rearrangement, or ring transformation, has on the size of the heterocyclic ring. A. REARRANGEMENTS WITHOUT ALTERATION OF RINGSIZE The Dimroth rearrangement of iminoquinazolinones and thiones has been known for some time (see Armarego,2 p.

Pozharliev and K. Zakharieva, Zzu. Otd. W i m . Nauki, Bulg. Akad. Nauk. 2, 341 (1969) [ C A 72, 78121 (1970)l. A. R. Katritzky, M. R. Nesbit, B. J. Kurtev, M. Lyapova, and I. G. Pojarlieff, Tetrahedron 25, 3807 (1969). Sec. VLB] QUINAZOLINES 43 azolinone 82 and its 3-methyl derivative gave the 4a-hydroperoxide 83 (R = OH) on standing in chloroform solution. 209Oxidation of 82 with hydrogen peroxide or monoperphthalic acid gave the 4a-hydroxy derivative, but the 1,Sa-double bond was also attacked to form the oxaziridinooctahydroquinazolinone 84.

32, 2681 (1967). E. E. Schweizer and S. V. DeVoe, J. Org. Chem. 40,144 (1975). 93 E. E. Schweizer, S. DeVoeGoff, and W. P. Murray, J. Org. Chem. 42,200 (1977). 94 A. Mendel, J. Heierocycl. Chem. 14, 153 (1977). 95 G. M. Coppola, G. E. Hardtmann, and 0. R. Hster, J. Org. Chem. 41, 825 (1976). 96 G. E. Patent 3936,453 (1976) [ C A 84, 164832 (1976)l. 91 92 Sec. D] 19 QUINAZOLINES whole process was not clear. ~~” + 0 0 D. QUINAZOLINE-2,4-DIONES The cyclization of o-ureidobenzoic esters to quinazoline-2,4-diones and 4-one-2-thiones, respectively, in aqueous alkali proceeded equally well with the N-hydroxy urea (X = 0)and thiourea (X = S)esters 28.

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