New PDF release: Advances in Heterocyclic Chemistry, Vol. 9

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 as a result of the Editorial Board, the writer, and the authors for his or her cooperation.

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37 E. G. Podrebarac and W. E. MoEwen,J. Org. Chem. 26, 1165 (1961). 38 H. W. Gibson, F. D. Popp, and A. Catala, J. Heterocyclic Chem. 1,251 (1964). 39 F. D. Popp and W. E. McEwen, J . Am. Chem. SOC. 80, 1181 (1958). 111. 4. F. D. 29-30 This advantage was noted despite the need of additional synthetic steps to convert the carbinol ester to a methylene group. 37I n the quinoline series the product has been converted to a compound having curariform activity. 33It should be pointed out, however, that the expected tertiary alcohols are available by reaction of Grignard reagents with Reissert compounds as noted below.

D. Popp, J. Org. Chem. 30, 3075 (1965). 111. 5. F. D. POPP anion (20) of 2-benzoyl-l,2-dihydroisoquinaldonitrile. 44The formation of 38 undoubtedly involves an initial addition of 20 to the carbonyl carbon N-CeHS (39) qN 0 II CHS-CH-O-C-C~HS (40) (4') atom of phenyl isocyanate to form 39 which then gives 38 via a cyclic intermediate in common with other similar reactions of Reissert compounds. b. Lactones. 32 Formation of 28 can be rationalized by attack of 20 on the lactone to give 40 which then gives 28 via a cyclic intermediate and decarboxylation.

Eng. Data 10, 79 (1965). 52 53 SEC. v. l’. 48It has been postulated that the initial dehydration converts 55 t o 59, an intermediate analogous to that (12) proposed for the hydrolysis of normal Reissert compounds. l The reaction of quinoline, benzoyl chloride, and silver phenylacetylide led to the formation of 6055which could be considered as a t & IC e CeH5-C=O (60) 55 H 5 Q,,6H5 I Ce&-C=O (61) T. Agawa and S. I. Miller, J . Am. Chem. SOC. 83, 449 (1961). 22 F. D. POPP [SEC. v. 1. being related to Reissert compound 1.

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


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