Advances in Heterocyclic Chemistry, Vol. 9 by A.R. Katritzky, A.J. Boulton (Eds.) PDF

By A.R. Katritzky, A.J. Boulton (Eds.)

ISBN-10: 0120206099

ISBN-13: 9780120206094

(from preface)The 9th quantity of Advances in Heterocyclic Chemistry contains surveys of the chemistry of the subsequent teams of heterocyclic compounds: 1,2,5-thiadiazoles (L. M. Weinstock and P. I. Pollack); 1,3,4-thiadiazoles (J. Sandstrom); pyridazines (M. Tisler and B. Stanovnik); Reissert compounds (F. D. Popp); phenothiazines (C. Bodea and that i. Silberg); and pyrrolopyridines (R. E. Willette).Suggestions are welcomed for contributions to destiny volumes; they need to be within the type of brief synopses.Thanks are because of the Editorial Board, the writer, and the authors for his or her cooperation.

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Kendall, J . Chem. , 3202 (1959). 5 1 G. E. Ficken and J. D. Kendall, J . Chem. , 584 (1961). 5 2 R. A. Abramovitch and J. G. Saha, Advan. Heterocyclic Chem. 6,333 (1966). 53 W. H. Perkin, Jr. and R. Robinson, J . Chem. 103, 1973 (1913). 54 R. G. Fargher and R. Furness, J . Chem. 107, 688 (1915). 48 38 R. E. WILLETTE [SEC. 111. c. of a small amount of acetic acid it led directly to the benzocarboline (25) in 63% yield. Interestingly, this procedure has not reportedly been tried on any pyridylhydrazine.

33 34 C. SEC. 111. ~~ Only nine substituted azaindoles4', 4 5 , 4 0 , 4 R , 4 g , 4ya and four a ~ a i n d o l e n i n e s ~ ~5 1, have been prepared by the Fischer cyclizstion. Abramovitch and Saha52discuss some of these reactions, pointing out the necessity of more vigorous conditions than are necessary to effect ring closure onto a benzene ring. Early attempts to cyclize 2-quinolylhydrazones of acetone,53 acetaldehyde, acetophenone, and pyruvic acid, and a number of 2-pyridylhydrazones,5 4 under a variety of conditions failed.

32 Alkylation of the phthalazine Reissert compound (6) with methyl iodide proceeded normally to give l-methylphthalazine. 3 . 33 Thus benzaldehyde, l-benzoyl-l,2-dihydroquinaldonitrile (7),and phenyllithium in ether-dioxan a t - 10" gave 29,33and benzaldehyde, 2-benzoyl-l,2-dihydroisoquinaldonitrile(S), and phenyllithium in ether-dioxan a t - 10"3 3 (or sodium hydride in refluxing H. W. Gibson, F. D. Popp, and A. C. Heterocyclic Chem. 3 , 9 9 (1966). F. D. Popp, H. W. Gibson, and A. C. Noble, J .

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Advances in Heterocyclic Chemistry, Vol. 9 by A.R. Katritzky, A.J. Boulton (Eds.)


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