A.R. Katritzky, A.J. Boulton (Eds.)'s Advances in Heterocyclic Chemistry, Vol. 9 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 comprises 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 kind 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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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.

Chemical Properties . A. General . B. Reduction and Oxidation . C. Electrophilic Substitution . D. Nucleophilic Substitution . E. Reactions Involving the Nitrogen Atoms F. Reactions Involving Side Chains . V. Physical Properties . A. Ionization Constants . B. Spectra . C. Miscellaneous . VI. Biological Properties. . . . . . . . . . . . 27 28 29 29 34 36 42 44 51 54 56 56 58 60 65 65 70 79 79 82 102 103 I. Introduction I n 1885, Fischer and Tauberl reported that a sublimate formed during the decomposition of harminic acid, an oxidation product of the alkaloid harmine.

32 J. M.. Wefer and F. D. Popp, J . Org. Chem. 32, 1999 (1967). 33 L. R. Welters, N. T. Iyer, and W. E. McEwen, J . A m . Chem. SOC. 80, 1177 (1958). 111. 1 13 REISSERT COMPOUNDS 0 qN 0 m - o - ( ! - C6H5 c6H5 H-C-0-C- I1 C6H5 I CBH5 (30) (29) benzene34 or sodium hydride in dimethylformamide a t room temperaturez7)gave 30. 33 A similar mechanism can be used for the formation of 30. It is of interest to note that in this case reaction of the anion (19) of the quinoline Reissert compound takes place in the 2-position.

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


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