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 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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Extra info for Advances in Heterocyclic Chemistry, Vol. 9
Similar reactions were reported recently starting with 2-methyl-7 azaindole. ' O The intermediate 2-methyl-7-azaindoline was used to prepare 5-hydroxy-, 5-methoxy-, 5-benzyloxy-, and 5-dimethylamino2 -methyl- 7 -azaindole. 6BM. M. Robison, F. P. Butler, and B. L. Robison, J. A m . Chem. 79, 2573 (1957). 69 M. M. Robison, B. L. Robison, and F. P. Butler, J . A m . Chem. , Netherland Patent 6,510,648 (1966); Chem. Abstr. 65, (1959). 13711 (1966). 111. ] MONOAZAINDOLES: THE PYRROLOPYRIDINES 45 This sequence is useful for preparing compounds inaccessible by other routes.
Patterson, L. T. Capell, and D. F. , p. 166. Am. Chem. , 1960. 10 A. A. loa The editors of the Journal of the Chemical Xociety prefer to use the diazaindene nomenclature, according to which compound 2 is 1,7diazaindene, etc. I n the present review the azaindole nomenclature is used. I n addition to being the most widely adopted and more concise, i t lends to a more convenient method of naming azalogs of known compounds, such as 7-azatryptophan. (3) (4) 111. Synthesis A. VIA THE MADELUNG SYNTHESIS The most successful method for preparing azaindoles has been the Madelung synthesis, which involves a base-catalyzed cyclization of o-acylaminotoluenes or picolines.
V. 1 O 23 REISSERT COMPOUNDS a t N H CN Q+ZN-C6H5 NC I CeHs--b=N-C6Hs CsHe-C=N-CaHs (64) (65) (66) 2. 59 As is typical of the Reissert compounds, these three compounds lack absorption peaks in the region 22002400 cm-'. To further the analogy t o Reissert compounds, acidcatalyzed hydrolysis of 64, 65, and 66 gave benzaldehyde. Picolinic acid, quinaldic acid, and isoquinaldic acid, respectively, as well as aniline, are also obtained from the hydrolysis. Nitrobenzene oxidation of the three compounds gave pyridine-2-carboxamide, quinaldonitrile, and isoquinaldonitrile, respectively.