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

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

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

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S, 2698 (1914)l. The situation was resolved by A. E. Tschitschibabin [Chern. Ber. 60, 1607 (1927)l who suggested that the name “ indolizine ” be adopted for these pyrrolo[1,2-a]pyridines and ‘‘ pyrindol ” be reserved for the azaindoles. 11 W. Madelung, Chern. Ber. 45, 1128 (1912). 12 P. L. Julian, E. W. Meyer, and H. C. Printy, in “Heterocyclic Compounds” (R. C. ), Vol. 3, p. 16. Wiley, New York, 1952. 111. A. R. E. WILLETTE TABLE I AZAINDOLES OBTAINED VIA Azaindole Substituent 4 4 4 4 4 2-Me 5-Me 2,5-Dimethyl 2-Ph, 5-Me 5 5 6 6 6 6 7 7 7 7 7 7 7 a - - 2-Me 2-Me 2-Ph 2 4 2-pyridyl) 2-(4-pyridyl) - 2-Me 2-Et 3-Me 4-Me 5-Me 6-Me THE MADELUNGSYNTHESIS Yield (%) 20,-,10a ca.

1860 (1966). F. D. Popp and H. W. Gibson, J . Heterocyclic Chem. 1, 51 (1964). L. R. Walters, I. C. Mineo, and R. S. Kripowicz, J . Org. Chem. 29,980 (1964). 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.

Parrick, Can. J . Chem. 43, 296 (1965). 46 A. H. Kelly and J. Parrick, Can. J . Chem. 44, 2455 (1966). 47 L. N. Yakhontov, E. V. Pronina, and M. V. Rubtsov, Dokl. Akad. Nauk SSSR 169, 361 (1966); R o c . A c d . Sci. USSR, Chem. Sect. ) 44 169, 705 (1966). Deutsche Gold- und Silver-Scheideanstalt vorm. Roessler, British Patent 259,982 (1925); Chem. Zentr. 991, 2311 (1928). Curiously, this patent does not appear to have been abstracted by Chem. Abstr. However, all the compounds, except the azaindoles, did appear in French Patent 641,422 (1926) ; Chem.

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