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 contains surveys of the chemistry of the next 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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Chem. 30, 2531 (1965). 16 J . C. Clayton and J. Kenyon, J. Chem. , 2962 (1950). , Netherlands Patent 6,414,916 (1965);Chem. Abstr. 64, 8152 (1966). 17 M. Protiva, J. 0. Jilek, Z. J. VejdBlek, and 0. Exner, Chem. L b t y 46, 551 (1952); Chem. Abstr. 48, 2710 (1954). 18 S. Okuda and M. M. Robison, J. Org. Chem. 24, 1008 (1959). 1 9 E. Koenigs and A. Fulde, Chem. Bey. 60, 2106 (1927). 20 W. Herz and D. R. K. Murty, J. Org. Chem. 25, 2242 (1960). 20a M. Hooper, D. A. Patterson, and D. 0. Wibberley, J.

VIA THE FISCHER INDOLE SYNTHESIS The synthesis of azaindoles by the Fischer indole synthesis has been tried more often than by any other method. It has given varied results, with over thirty successful ring closures of pyridyl- or quinolylhydrazones reported. Most of these have led to carboline derivaA. Albert, J. Chem. ,1790 (1960). R. Hauser and G. A. Reynolds, J. Org. Chem. 15, 1224 (1950). 35 C. C. Price and R . M. Roberts, J . A m . Chem. SOC. 68, 1204 (1946). 36 J. T. A d a m , C. K . Bradsher, D.

Am. Chern. Soc. 63, 2024 (1941). 1x1. A. R. E . WILLETTE The first significant improvement in the Madelung approach to azaindoles was introduced by Robison and Robison22who obtained 7-azaindole (2) in 52% yield by using sodium anilide as the base together with potassium formate, another of Tyson's26modifications. 18 Herz and Murty28were unable t o repeat this last cyclization. Also, they20 recovered 3-amino-4picoline (11, R = H) (25-40 yo)on treating the formamide (5, R = H) with sodium anilide, sodium ethoxide, or the sodium salt of the amine (11, R = H ) .

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