Advances in Heterocyclic Chemistry, Vol. 24 - download pdf or read online

By A.R. Katritzky

ISBN-10: 0120206242

ISBN-13: 9780120206247

(from preface)This quantity makes an enormous contribution to the method of up-dating previous volumes that we have got initiated. Seven of the 9 chapters are dedicated to this goal and to any extent further we intend to up-date chapters from 10 to fifteen years after their visual appeal, only if massive paintings has been performed within the region covered.Five chapters were up-dated via the authors of the unique chapters that seemed in prior volumes, as follows: Quinazolines, via W. L. F. Armarego (the unique bankruptcy seemed in quantity 1), 3-membered earrings with Heteroatoms, by way of E. Schmitz (Volume 2), Physicochemical points of Purines, by means of J. H. Lister (Volume 6), Reis-sert Compounds, via F. D. Popp (Volume 9), and Pyridazines, by means of M. Tiffler and B. Stanovnik (Volume 9).Two different chapters up-date topics coated in previous volumes, yet via assorted authors: Selenium-Nitrogen Heterocycles, via I. Lalezari, A. Shafiee, and M. Yalpani, which up-dates the contribution via Bulka in quantity 2 on Selenazole Chemistry, and Pyrrolizidines, by way of D. J. Robins, which up-dates the contribution via Kochetkov and Likhosherstov in quantity 5.Finally, chapters care for considerably new issues: Benzo[c]cin-nolines, via J. W. Barton, and 1, 4-Thiazines, by means of R. J. Stoodley.

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Allison, R . D. Chambers, J. A. H. MacBride, and W. K . R. , 1979 (1970). 28 W. L. F. ARMAREGO [Sec. ' 38 A useful reagent for converting quinazolin-2(1H ) - and 4(3H)-ones into 2- and 4-aminoquinazolines in one step was diphenylphosphordiamidate. An Arbuzov reaction occurred between trialkylphosphite and chloroquinazolines, and dialkyl 4-quinazolinylphosphonates were formed. The 4chlorine atom was more reactive than the 2-chlorine atom, and the phosphonate group could be displaced by methoxide and a m i n e ~ .

Mathis, Bull. , 2615 (1970). 160 . I. B. Hester, J. Org. Chem. 39, 2137 (1974). 154 32 [Sec. V W. L. F. ARMAREGO obtained from mixing o-aminoacetophenone and methazonic acid turned 3-oxide (59 : R' = out to be 4-methyl-2-nitromethyl-l,2-dihydroquinazoline CH,NO,; R2 = Me). This dihydro compound eliminated nitromethane on melting and formed 4-methylquinazoline 3-oxide. 61 An earlier proposed structure for the bis oxime of N-acetylisatin was shown to be erroneous. ' 6 2 The hydroxamic acid (60) underwent a Lossen reaction to form the 4-isocyanato derivative, which cyclized to the oxadiazoloquinazoline 61.

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.

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

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